[ CAS No. 65202-58-6 ] {[proInfo.proName]}

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Quality Control of [ 65202-58-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 65202-58-6 ]

SDS Specification

Alternatived Products of [ 65202-58-6 ]

Product Details of [ 65202-58-6 ]

CAS No. :	65202-58-6	MDL No. :	MFCD09831907
Formula :	C₅H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RACIHBXDZONTQJ-UHFFFAOYSA-N
M.W :	173.01	Pubchem ID :	11959086
Synonyms :

Calculated chemistry of [ 65202-58-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.7
TPSA :	25.78 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	1.27
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	1.12
Log Po/w (SILICOS-IT) :	2.08
Consensus Log Po/w :	1.56

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.27
Solubility :	0.934 mg/ml ; 0.0054 mol/l
Class :	Soluble
Log S (Ali) :	-1.41
Solubility :	6.72 mg/ml ; 0.0389 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.89
Solubility :	0.224 mg/ml ; 0.0013 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 65202-58-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 65202-58-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 65202-58-6 ]
Downstream synthetic route of [ 65202-58-6 ]

[ 65202-58-6 ] Synthesis Path-Upstream 1~5

1
[ 13327-27-0 ]
[ 65202-58-6 ]

Yield	Reaction Conditions	Operation in experiment
31%	at 70℃;	A mixture of Example 13B (18g, 163.44mmol) and phosphorus oxybromide (93.8g, 327.6mmol) was stirred at70°C overnight. The mixture was cooled to 40°C, poured into ice-water, quenched with saturated sodium bicarbonate(20mL) and extracted with dichloromethane (100mL 3 3). The organic layers were combined, dried over anhydroussodium sulfate, filtered and evaporated to give the title compound, 3-bromo-6-methylpyridazine (8g, yield 31percent). LCMS(ESI) m/z: 173[M+1]+. 1H NMR (CHLOROFORM-d, BrukerAvance 400MHz): ppm 7.86-7.88 (d, 1H, J = 8 Hz), 7.52-7.54(d, 1H, J = 8 Hz), 2.55(s, 3H).

Reference： [1] Patent: EP3333157, 2018, A1, . Location in patent: Paragraph 0136; 0137
[2] Patent: WO2010/36998, 2010, A2, . Location in patent: Page/Page column 184

2
[ 157200-06-1 ]
[ 65202-58-6 ]

Reference： [1] Patent: US6265434, 2001, B1,

3
[ 539-88-8 ]
[ 65202-58-6 ]

Reference： [1] Patent: EP3333157, 2018, A1,

4
[ 94248-99-4 ]
[ 65202-58-6 ]

Reference： [1] Chemische Berichte, 1948, vol. 81, p. 1,10

5
[ 5157-08-4 ]
[ 65202-58-6 ]

Reference： [1] Patent: EP3333157, 2018, A1,

[ 65202-58-6 ] Synthesis Path-Downstream 1~19

1
[ 65202-58-6 ]
[ 119405-65-1 ]
3-Methyl-6-thiophen-3-yl-pyridazine [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1995,p. 2422 - 2434

2
[ 5382-16-1 ]
[ 65202-58-6 ]
[ 152665-35-5 ]

Yield	Reaction Conditions	Operation in experiment
24%	With N-ethyl-N,N-diisopropylamine;	EXAMPLE 5 Following a procedure similar to that of Example 3, 81 millimoles of <strong>[65202-58-6]6-methyl-3-bromopyridazine</strong> was combined with 16 mL DIPEA and 163 mmoles of 4-hydroxypiperidine and heated to 120 for 16 hours to obtain 6-methyl-3-(4-hydroxy-1-piperdinyl)pyridazine (Formula IV: Y=bond, R=CH3) in 24% yield. 6.8 Mmols of the latter and 7.4 mmoles of 2-methyl-5-(4-hydroxy-3,5-dimethyl phenyl)-2H-tetrazole (Formula III: R2 =R3 =R4 =CH3) were reacted with equimolar amounts of DEAD and TPP essentially as described above in Example 1c.

Reference： [1]Patent: US5242924,1993,A

3
[ 65202-58-6 ]
aq. NH₄Cl [ No CAS ]
[ 7648-30-8 ]
[ 12775-96-1 ]
ethyl difluoro(6-methylpyridazin-3-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; dimethyl sulfoxide;	Step B Ethyl difluoro(6-methylpyridazin-3-yl)acetate This procedure is derived from the general method of T. Taguchi, et al. (Tetrahedron Lett., 1986,27,6103-6106). Ethyl difluoroiodoacetate (0.355 mL, 651 mg, 2.60 mmol) was added to a rapidly stirred suspension of copper powder (333 mg, 5.24 mmol) in DMSO (6.5 mL) at RT. After 50 min., <strong>[65202-58-6]3-bromo-6-methylpyridazine</strong> (300 mg, 1.73 mmol) was added in DMSO (1.0 mL). After 20 h, the mixture was transferred to a separatory funnel containing water (25 mL) and saturated aq. NH4Cl (25 mL), and extracted with EtOAc (2*50 mL). The organic extracts were washed with saturated aq. NaCl, dried (Na2SO4), decanted, and evaporated. Purification by flash column chromatography on silica gel, eluding with 70:30 v/v hexanes/EtOAc, gave 363 mg of the title compound as an amber liquid. For the title compound: 1H NMR (500 MHz, CDCl3) delta 7.79 (d, J=9, 1H), 7.53 (d, J=9, 1H), 4.43 (q, J=7, 2H), 2.82 (s, 3H), 1.38 (t, J=7, 3H).

Reference： [1]Patent: US6265434,2001,B1

4
[ 157200-06-1 ]
[ 65202-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; hydrogen bromide; In acetic acid;	Step A 3-Bromo-6-methylpyridazine A solution (3.0 mL) containing 30%HBr in acetic acid was added to 3-(trifluoromethanesulfonyloxy)-6-methylpyridazine (prepared as described by M. Rohr, et al., Heterocycles, 1996, 43, 1459-64) and the mixture was heated in a 100 C. oil bath for 2.5 h. The mixture was cooled in an ice bath, adjusted to pH >=9 (as determined using pH paper) by the careful addition of 20% aqueous NaOH, and extracted with ether (3*20 mL). The organic layers were dried (Na2SO4), decanted, and evaporated to give title compound as 359 mg of pale tan crystals. For the title compound: 1H NMR (500 MHz, CDCl3) delta 7.56 (d, J=9, 1H), 7.22 (d, J=9, 1H), 2.70 (s, 3H).

Reference： [1]Patent: US6265434,2001,B1

5
[ 65202-58-6 ]
[ 1000798-21-9 ]
6,6-dimethyl-2-[6-(6-methylpyridazin-3-yl)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5H)-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4700 - 4704

6
[ 65202-58-6 ]
potassium vinyltrifluoroborate [ No CAS ]
[ 848774-92-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;triphenylphosphine; palladium dichloride; In tetrahydrofuran; water; at 75 - 80℃; for 22h;Inert atmosphere;	Potassium vinyltrifluoroborate (Aldrich, 1.71 g, 12.7 mmol), 3-bromo-6- methylpyridazine (Example 148A, 1.95 g, 11.3 mmol) and triphenylphosphine (0.18 g, 0.67 mmol) were added at room temperature to a solution Of Cs2CO3 (10.1 g, 31.0 mmol) in water (9.5 mL). Tetrahydrofuran (85 mL) was added, and the reaction flask was evacuated and purged with nitrogen (3 cycles). PdCl2 (50 mg, 0.28 mmol) was added, and the reaction flask was again evacuated and purged with nitrogen (3 cycles), then heated under nitrogen at 75-80 0C for 22 hours. The mixture was cooled to room temperature and the aqueous layer was separated and extracted with ethyl ether (3chi50 mL). The combined organic phase was concentrated to a volume of approximately 5 mL, and the residue was purified by flash chromatography (80 g silica, eluted with hexanes-ethyl acetate, 100:0 - 90:10): 1H NMR (300 MHz, methanol-^) delta ppm 2.71 (s, 3 H) 5.63 (d, J=I 1.2 Hz, 1 H) 6.18 (d, J=18.3 Hz, 1 H) 7.04 (dd, J=17.8, 11.0 Hz, 1 H) 7.23 - 7.34 (m, J=8.8 Hz, 1 H) 7.49 (d, J=8.8 Hz, 1 H).

Reference： [1]Patent: WO2010/36998,2010,A2 .Location in patent: Page/Page column 183-184

7
[ 13327-27-0 ]
[ 65202-58-6 ]

Yield	Reaction Conditions	Operation in experiment
31%	With phosphorus(V) oxybromide; at 70℃;	A mixture of Example 13B (18g, 163.44mmol) and phosphorus oxybromide (93.8g, 327.6mmol) was stirred at70C overnight. The mixture was cooled to 40C, poured into ice-water, quenched with saturated sodium bicarbonate(20mL) and extracted with dichloromethane (100mL 3 3). The organic layers were combined, dried over anhydroussodium sulfate, filtered and evaporated to give the title compound, 3-bromo-6-methylpyridazine (8g, yield 31%). LCMS(ESI) m/z: 173[M+1]+. 1H NMR (CHLOROFORM-d, BrukerAvance 400MHz): ppm 7.86-7.88 (d, 1H, J = 8 Hz), 7.52-7.54(d, 1H, J = 8 Hz), 2.55(s, 3H).
		6-Methylpyridazin-3(2H)-one (Alfa, 2.5 g, 22.70 mmol) and phosphorus oxybromide (Aldrich, 16.27 g, 56.8 mmol) were heated at 90 C under a nitrogen atmosphere for 1.5 hours. After cooling, the mixture was poured onto ice (100 g), neutralized with sodium bicarbonate, and the aqueous phase was extracted with CH2Cl2 (3chi30 mL). The combined organic phase was washed with 5% NaHCO3, brine, dried (Na2SO4) and concentrated. The residue was dissolved in hot ethyl acetate and washed through a plug of silica gel, eluting with ethyl acetate and concentrated. MS (DCI/NH3) m/z 172 (M+H)+, 190 (M+NH4)+.

Reference： [1]Patent: EP3333157,2018,A1 .Location in patent: Paragraph 0136; 0137
[2]Patent: WO2010/36998,2010,A2 .Location in patent: Page/Page column 184

8
[ 65202-58-6 ]
methyl 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(2-aminoethylamino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate dihydrochloride [ No CAS ]
[ 76-05-1 ]
4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-(6-methylpyridazin-3-ylamino)ethylamino)-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid bis-trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.3%		Example 194 Preparation of 4-((lR,3aS,5aR,5bR,7aR, l laS, l lbR,13aR,13bR)-5a,5b,8,8,l la- pentamethyl-3 a-(2-(6-methylpyridazin-3 -ylamino)ethylamino)- 1 -(prop- 1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8, l l, l la, l lb, 12, 13, 13a, 13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acid.In a 1 dram vial under nitrogen were combined (2R)-l-[(lR)-l-[bis(l, l- dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene (CASNo. 158923- 11-6) (2.52 mg, 4.55 muiotaetaomicron), palladium(II) acetate (1.02 mg, 4.55 muiotaetaomicron) and dry DME (0.5 ml). The contents of the vial were stirred for 10 min, and were then added all at once to a separate mixture of <strong>[65202-58-6]3-bromo-6-methylpyridazine</strong> (0.017 g, 0.100 mmol) and sodium tert-butoxide, 2.0M solution in THF (0.200 mL, 0.400 mmol) in dry DME (0.500 mL) contained in a separate 1 dram vial. The resulting mixture was allowed to stir very briefly (1 min) before solid methyl 4-((lR,3aS,5aR,5bR,7aR, l laS, l lbR, 13aR,13bR)-3a-(2-aminoethylamino)- 5a,5b,8,8, 1 1 a-pentamethyl- 1 -(prop- 1 -en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8, l l, l la, l lb, 12, 13, 13a, 13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate bis HC1 salt (0.060 g, 0.091 mmol) was added in one portion. The mixture was heated to 1 10 C overnight. Iterative purification of the crude mixture by reverse phase preparative HPLC first using Prep HPLC Method 9 and then repurification by Prep HPLC Method 10 gave the title compound (0.0070 g, 8.3% yield) as a white glassy solid bis TFA salt. LCMS: m/e 665.5 (M+H)+, 2.22 min (method 11). XH NMR (500 MHz, 1 : 1 mixture of CDC13 and MeOD, MeOD lock) delta ppm 7.90 (d, J=8.5 Hz, 2H), 7.49 - 7.42 (m, 1H), 7.32 - 7.23 (m, 1H), 7.18 (d, J=8.2 Hz, 2H), 5.27 (dd, J=6.0, 1.4 Hz, 1H), 4.88 (br. s., 1H), 4.72 (br. s., 1H), 3.94 - 3.84 (m, 1H), 3.84 - 3.73 (m, 1H), 3.26 - 3.13 (m, 1H), 2.84 (d, J=12.5 Hz, 1H), 2.57 (s, 3H), 2.12 (dd, J=16.9, 6.3 Hz, 1H), 2.05 (d, J=15.6 Hz, 1H), 2.01 - 1.91 (m, 2H), 1.91 - 1.74 (m, 2H), 1.70 (s, 3H), 1.69 - 1.59 (m, 2H), 1.59 - 1.43 (m, 4H), 1.43 - 1.28 (m, 4H), 1.28 - 1.18 (m, 4H), 1.18 - 1.06 (m, 2H), 1.05 (s, 3H), 0.99 (s, 3H), 0.97 (s, 3H), 0.92 (s, 3H), 0.92 - 0.89 (m, 3H).

Reference： [1]Patent: WO2012/106190,2012,A1 .Location in patent: Page/Page column 330-332

9
[ 65202-58-6 ]
5-fluoro-3-(2-methoxyethyl)-1H-benzimidazol-2-one [ No CAS ]
5-fluoro-3-(2-methoxyethyl)-1-(6-methylpyridazin-3-yl)benzimidazol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium carbonate; In dimethyl sulfoxide; at 80℃; for 3h;	Prepared by the reaction of 5-fluoro-3-(2-methoxyethyl)-1 H-benzimidazol-2-one (100 mg, 0.48 mmol) with <strong>[65202-58-6]3-bromo-6-methylpyridazine</strong> (90.54 mg, 0.52 mmol), potassiumcarbonate (197 mg, 1.43 mmol), copper iodide (9.1 mg, 0.05 mmol) and trans-A/,/V-20 dimethylcyclohexane-1,2-diamine (0.02 ml_, 0.10 mmol) in DMSO (2.5 ml.) at 80 C for 3 h.The desired product 5-fluoro-3-(2-methoxyethyl)-1-(6-methylpyridazin-3-yl)benzimidazol-2-one was isolated as a white solid (41 mg, 0.136 mmol, 28%).[00499] 1H NMR (300MHz, DMSO-d6) Shift = 8.29 (d, J=9.0 Hz, 1H), 7.97 (dd, J=4.9,8.9 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.35 (dd, J=2.5, 9.1 Hz, 1H), 6.98 (ddd, J=2.6, 8.9, 9.925 Hz, 1 H), 4.11 (t, J=5.3 Hz, 2H), 3.67 (t, J=5.3 Hz, 2H), 3.26 (s, 3H), 2.68 (s, 3H)

Reference： [1]Patent: WO2016/97749,2016,A1 .Location in patent: Paragraph 00498; 00499

10
[ 65202-58-6 ]
[ 348133-45-9 ]
5-fluoro-3-methyl-1-(6-methylpyridazin-3-yl)benzimidazol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium carbonate; In 1,4-dioxane; at 80℃; for 16h;	Prepared by the reaction of 5-fluoro-3-methyl-1 /-/-benzimidazol-2-one (150 mg, 0.90 mmol) with <strong>[65202-58-6]3-bromo-6-methylpyridazine</strong> (172 mg, 0.99 mmol), potassium carbonate37415 mg, 2.71 mmol), copper iodide (17 mg, 0.09 mmol) and trans-A/,/V-dimethylcyclohexane-1,2-diamine (0.03 ml_, 0.18 mmol) in 1,4-dioxane (2.5 ml.) at 80 C for 16 h. The desired product5-fluoro-3-methyl-1 -(6-methylpyridazin-3-yl)benzimidazol-2-one was isolated as a yellow solid(180 mg, 0.697 mmol, 77%).[00502] 1H NMR (300MHz, DMSO-d6) Shift = 8.30 (d, J=9.0 Hz, 1H), 7.99 (dd, J=4.9,20 8.9 Hz, 1H), 7.78 (d, J=9.1 Hz, 1H), 7.31 (dd, J=2.5, 8.9 Hz, 1H), 6.98 (ddd, J=2.6, 8.9, 10.0Hz, 1 H), 3.41 (s, 3H), 2.67 (s, 3H)

Reference： [1]Patent: WO2016/97749,2016,A1 .Location in patent: Paragraph 00501; 00502

11
[ 65202-58-6 ]
methyl 3-hydroxy-5-(5-methyl-1,3-thiazol-2-yl)benzoate [ No CAS ]
3-[(6-methylpyridazin-3-yl)oxy]-5-(5-methyl-1,3-thiazol-2-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		A solution of Intermediate 3 (130 mg, 0.52 mmol), <strong>[65202-58-6]3-bromo-6-methyl-pyridazine</strong>(135 mg, 0.78 mmol) and caesium carbonate (340 mg, 1.04 mmol) in DMF (2.5 mL)was heated in the microwave to 120C for 45 mm, then for a further 20 mm at thesame temperature. The reaction mixture was concentrated under reduced pressureand the residue taken up in methanol (5 mL) and treated with 1M LiCH (2.5 mL). After 1 .5h, the reaction was concentrated to remove the organics, before being diluted with water (10 mL) and extracted with EtOAc (2 x 10 mL). The aqueous layer was acidified to -pH 4 with 2M HCI, the extracted with DCM (3 x 10 mL). Thecombined organics were dried over MgSO4, filtered and concentrated under reduced pressure to afford 143 mg (73% yield) of the title compound as brown gum. 1H NMR (500 MHz, Chloroform-d): 6 [ppm] 8.48 (5, 1H), 8.06 (5, 1H), 8.00 - 7.96 (m, 1H), 7.59 (5, 1H), 7.42 (d, J = 9.0 Hz, 1H), 7.19 (d, J = 9.0 Hz, 1H), 2.70 (d, J = 7.7 Hz, 3H), 2.53 (5, 3H).LCMS (Analytical Method A) Rt = 1.01 mm, MS (ESIpos): m/z = 328.05 (M+H).

Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 199; 200

12
[ 65202-58-6 ]
tert-butyl 2-(3-acetyl-5-hydroxy-1H-indazol-1-yl)acetate [ No CAS ]
tert-butyl 2-(3-acetyl-5-((6-methylpyridazin-3-yl)oxy)-1H-indazol-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 24h;Inert atmosphere; Sealed tube;	Step I : tert-Butyl 2-(3-acetyl-5-((6-raethylpyridazin-3-yl)oxy)-lH-indazol-'l-yl)acetate {237} [0737] A mixture of tert-butyl 2-(3-acetyl-5-hydroxy-l H-indazol-l -yl)acetate (1 equiv), <strong>[65202-58-6]3-bromo-6-methylpyridazine</strong> (1.1 equiv), K2CO3 (3 equivj and 18-Crown-6 (1 equiv) in DMF (10 vol) under argon, the pressure vessel was sealed and heated at 100 C for 24 h. The reaction mixture was cooled to rt and diluted with water, then extracted with DCM. The organic layer was washed with brine, dried over anhydrous NaiSCXt, filtered, and then concentrated. The residue was purified by column chromatography on silica gel (EtOAc/DCM) to give compound 237.

Reference： [1]Patent: WO2017/35355,2017,A1 .Location in patent: Paragraph 0737

13
[ 539-88-8 ]
[ 65202-58-6 ]