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Chemical Structure| 271-34-1 Chemical Structure| 271-34-1
Chemical Structure| 271-34-1

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CAS No.: 271-34-1

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5-Azaindole is a biochemical reagent that can serve as a biomaterial or organic compound for life science-related research.

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Product Details of 5-Azaindole

CAS No. :271-34-1
Formula : C7H6N2
M.W : 118.14
SMILES Code : C1=C[NH]C2=C1C=NC=C2
MDL No. :MFCD00955936
InChI Key :SRSKXJVMVSSSHB-UHFFFAOYSA-N
Pubchem ID :9220

Safety of 5-Azaindole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P280-P271-P302+P352-P312-P304+P340-P305+P351+P338-P362+P364-P403+P233-P501

Application In Synthesis of 5-Azaindole

* 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 [ 271-34-1 ]
  • Downstream synthetic route of [ 271-34-1 ]

[ 271-34-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 271-34-1 ]
  • [ 98-09-9 ]
  • [ 109113-39-5 ]
YieldReaction ConditionsOperation in experiment
69.4%
Stage #1: With sodium hydride In mineral oil at 0℃; for 0.5 h;
Stage #2: at 0 - 20℃; for 1 h; 		To a solution of lH-pyrrolo[3,2-c]pyridine (LXXIV) (1 g, 8.47 mmol, 1.0 eq) in THF (10 mL) was added NaH (60percent in mineral oil) (0.24 g, 10.2 mmol, 1.2 eq) at 0°C. The mixture was stirred at 0°C for 0.5 h. PhS02Cl (LXXV) (1.80 g, 10.2 mmol, 1.2 eq) was then added to the solution at 0°C. The reaction was warmed to room temperature and stirred for 1 h. Aqueous NaHCCb (30 mL) was added and then extracted with EtOAc (x 3). The organic phase was combined and dried over Na2SC>4. Removal solvents under reduced pressure gave l -(phenylsulfonyl)- lH- pyrrolo[3,2-c]pyridine (LXXVI) as a yellow solid. (1.52 g, 5.88 mmol, 69.4percent yield) . NMR (CDCI3, 400 MHz) δ ppm 6.75 (d, J=3.6Hz, 1H), 7.48 (t, J=8Hz, 2H), 7.55 - 7.61 (m, 2H), 7.89 - 7.93 (m, 3H), 8.49 (d, J=6Hz, 1H), 8.88 (s, 1H); ESIMS found for C13H10N2O2S mlz 259.1 (M+H).
69.4%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5 h;
Stage #2: at 0 - 20℃; for 1 h; 		To a solution of lH-pyrrolo[3,2-c]pyridine (LXXIV) (1 g, 8.47 mmol, 1.0 eq) in THF (10 mL) was added NaH (60percent in mineral oil) (0.24 g, 10.2 mmol, 1.2 eq) at 0°C. The mixture was stirred at 0°C for 0.5 h. PhS02Cl (LXXV) (1.80 g, 10.2 mmol, 1.2 eq) was then added to the solution at 0°C. The reaction was warmed to room temperature and stirred for 1 h. Aqueous NaHCC (30 mL) was added and then extracted with EtOAc (x 3). The organic phase was combined and dried over Na2SC>4. Removal solvents under reduced pressure gave 1 - (phenylsulfonyl)-lH-pyrrolo[3,2-c]pyridine (LXXVI) as a yellow solid. (1.52 g, 5.88 mmol, 69.4percent yield). NMR (CDCI3, 400 MHz) δ ppm 6.75 (d, J=3.6Hz, 1H), 7.48 (t, J=8Hz, 2H), 7.55 - 7.61 (m, 2H), 7.89 - 7.93 (m, 3H), 8.49 (d, J=6Hz, 1H), 8.88 (s, 1H); ESIMS found for Ci3HioN202S mlz 259.1 (M+H).
69.4%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5 h;
Stage #2: at 0 - 20℃; for 1 h; 		To a solution of lH-pyrrolo[3,2-c]pyridine (XCI) (1 g, 8.47 mmol, 1.0 eq) in THF (10 mL) was added NaH (60percent in mineral oil) (0.24 g, 10.2 mmol, 1.2 eq) at 0°C. The mixture was stirred at 0°C for 0.5 h. PhS02Cl (XCII) (1.80 g, 10.2 mmol, 1.2 eq) was then added to the solution at 0°C. The reaction was warmed to room temperature and stirred for 1 h. Aqueous NaHCC>3 (30 mL) was added and then extracted with EtOAc (x 3). The organic phase was combined and dried over Na2SC>4. Removal solvents under reduced pressure gave l-(phenylsulfonyl)-lH- pyrrolo[3,2-c]pyridine (XCIII) as a yellow solid. (1.52 g, 5.88 mmol, 69.4percent yield). NMR (CDC , 400 MHz) δ ppm 6.75 (d, J=3.6Hz, 1H), 7.48 (t, J=8Hz, 2H), 7.55 - 7.61 (m, 2H), 7.89 - 7.93 (m, 3H), 8.49 (d, J=6Hz, 1H), 8.88 (s, 1H); ESIMS found for C13H10N2O2S mlz 259.1 (M+H).
69.4%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5 h; 		Step 1 [0675] To a solution of lH-pyrrolo[3,2-c]pyridine (LXXIV) (1 g, 8.47 mmol, 1.0 eq) in THF (10 mL) was added NaH (60percent in mineral oil) (0.24 g, 10.2 mmol, 1.2 eq) at 0°C. The mixture was stirred at 0°C for 0.5 h. PhS02Cl (LXXV) ( 1.80 g, 10.2 mmol, 1.2 eq) was then added to the solution at 0°C. The reaction was warmed to room temperature and stirred for 1 h. Aqueous NaHCC^ (30 mL) was added and then extracted with EtOAc (x 3). The organic phase was combined and dried over Na2SC>4. Removal solvents under reduced pressure gave 1 - (phenylsulfonyl)-lH-pyrrolo[3,2-c]pyridine (LXXVI) as a yellow solid. (1.52 g, 5.88 mmol, 69.4percent yield). NMR (CDC13, 400 MHz) δ ppm 6.75 (d, J=3.6Hz, 1H), 7.48 (t, J=8Hz, 2H), 7.55 - 7.61 (m, 2H), 7.89 - 7.93 (m, 3H), 8.49 (d, J=6Hz, 1H), 8.88 (s, 1H); ESIMS found for C13H10N2O2S mlz 259.1 (M+H).

References: [1] Synthesis, 2005, # 20, p. 3581 - 3588.
[2] Patent: WO2017/23987, 2017, A1, . Location in patent: Paragraph 0675; 0676.
[3] Patent: WO2017/24003, 2017, A1, . Location in patent: Paragraph 0675; 0676.
[4] Patent: WO2017/24010, 2017, A1, . Location in patent: Paragraph 0622; 0623.
[5] Patent: WO2017/23984, 2017, A1, . Location in patent: Paragraph 0675.
[6] Tetrahedron, 1993, vol. 49, # 14, p. 2885 - 2914.
[7] Patent: WO2015/88045, 2015, A1, . Location in patent: Paragraph 0339; 0340.
[8] Patent: US2017/8885, 2017, A1, . Location in patent: Paragraph 0741-0742.
 

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