7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridine → 4-methoxy-7-(4-methyl-1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine

HRID 1157843Notes

Reaction equation

HRID 1157843 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[N:10][C:9](Br)=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[CH3:13][C:14]1[N:15]=[N:16][NH:17][CH:18]=1>>[CH3:1][O:2][C:3]1[CH:11]=[N:10][C:9]([N:17]2[CH:18]=[C:14]([CH3:13])[N:15]=[N:16]2)=[C:8]2[NH:7][CH:6]=[CH:5][C:4]=12

Participants

3

Reactant 2

HCID 207912447-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridineHCID 1784309184-methyl-1H-1,2,3-triazole

Product 1

HCID 596816714-methoxy-7-(4-methyl-1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine

Conditions

Temperature
130 °C

Procedure

4-Methoxy-7-bromo-6-azaindole (120 mg) was added in portions to a melted of 4-methyl-1,2,3-triazole (219 mg) under argon at 110-120° C. The mixture was heated to 130° C. and was stirred at 130° C. for 17 hours. The reaction mixture was cooled to room temperature and the resulting residue was purified by column chromatography using EtOAc/Hexane (6:4) mixture as eluent which afforded 4-methoxy-7-(4-methyl-1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine as a tan solid. 1H NMR (400 MHz, DMSO-D6): δ 2.38 (s, 3H), 4.01 (s, 3H), 6.66 (dd, 1H, J=2.9, 2.6), 7.53 (dd, 1H, J=2.9, 2.8), 7.70 (s, 1H), 8.62 (s, 1H), 11.78 (bs, 1H). MS: 230.3 (M++1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-a8528bc9920a43b4bf5d0114052dcd58
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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