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With N,N-dimethyl-formamide; phosphorus(V) oxybromide; at 20 - 110℃; for 3.08333h;
A total of 117 g of 5-80 was divided in 4 batches of 30 g×3 and 27 g×1 and treated with POBr3 (3 equiv.; 163 g×3 and 155 g×1) and a catalytic amount of DMF (15 ml) at rt (DMF was added carefully gas evolution). After 5 min. at room temperature, the solutions were heated at 110 C. for 3 hr. LC/MS showed starting material had been consumed. The reaction mixtures were allowed to cool to rt. The reaction flasks were placed in an ice bath; and then ice was added very slowly and carefully portionwise into the flask, gas evolution was due to HBr formation; the liquid and black solid that formed was poured into a beaker with ice. EtOAc was added and the mixture was then extracted several times with EtOAc. The organic layer was washed with saturated aq. NaHCO3; H2O and brine; dried over Na2SO4 and filtered. The product was dried in the pump overnight to provide 123 g of 6-80 as a brown solid (77% yield). [1498] Note: Reaction is completed within 1 h. [1499] 1HNMR(delta, CDCl3):8.52 (m, 1H), 7.93 (m, 1H).
77 - 97%
With phosphorus(V) oxybromide;N,N-dimethyl-formamide; at 20 - 110℃; for 3h;
A total of 117 g of intermediate 4 was divided in 4 batches of 30 g×3 and 27 g×1 and treated with POBr3 (3 equiv.; 163 g×3 and 155 g×1) and a catalytic amount of DMF (15 ml) at rt (DMF was added carefullygas evolution). After 5 min. at room temperature, the solutions were heated at 110 C. for 3 hr. LC/MS showed starting material had been consumed. The reaction mixtures were allowed to cool to rt. The reaction flasks were placed in an ice bath; and then ice was added very slowly and carefully portionwise into the flask, gas evolution was due to HBr formation; the liquid and black solid that formed was poured into a beaker with ice. EtOAc was added and the mixture was then extracted several times with EtOAc. The organic layer was washed with saturated aq. NaHCO3; H2O and brine; dried over Na2SO4 and filtered. The product was dried in the pump overnight to provide 123 g of intermediate 5 as a brown solid (77% yield). Note: Reaction is completed within 1 h. 1HNMR(delta, CDCl3):8.52 (m, 1H), 7.93 (m, 1H).
77%
With phosphorus(V) oxybromide;N,N-dimethyl-formamide; at 110℃; for 3h;
A total of 117 g of 5-80 was divided in 4 batches of 30 g×3 and 27 g×1 and treated with POBr3 (3 equiv.; 163 g×3 and 155 g×1) and a catalytic amount of DMF (15 ml) at rt (DMF was added carefully gas evolution). After 5 min. at room temperature, the solutions were heated at 110 C. for 3 hr. LC/MS showed starting material had been consumed. The reaction mixtures were allowed to cool to rt. The reaction flasks were placed in an ice bath; and then ice was added very slowly and carefully portionwise into the flask, gas evolution was due to HBr formation; the liquid and black solid that formed was poured into a beaker with ice. EtOAc was added and the mixture was then extracted several times with EtOAc. The organic layer was washed with saturated aq. NaHCO3; H2O and brine; dried over Na2SO4 and filtered. The product was dried in the pump overnight to provide 123 g of 6-80 as a brown solid (77% yield). Note: Reaction is completed within 1 h. 1HNMR(delta, CDCl3):8.52 (m, 1H), 7.93 (m, 1H).
With phosphorus(V) oxybromide; In DMF (N,N-dimethyl-formamide); at 110℃;
Intermediate 4,4-fluoro-7-bromo-6-azaindole, was prepared according to the following scheme: [CHEMMOL-00081] [0364] A) fuming HNO3, H2SO4; [0365] B) POBr3/DMF, 110 C.; [0366] C) vinylmagnesium bromide, THF, -78 C. -20 C. [0367] Intermediate 4 was isolated as a brownish solid. MS m/z: (M+H)+ calcd for C7H5BrFN2: 214.96; found 214.97. HPLC retention time: 1.28 minutes (column G).
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