4-Chloro-1H-pyrrolo[2,3-b]pyridine → 4-(4-bromo-3-methyl-1H-pyrazol-1-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 40876

Reaction equation

HRID 40876 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Br:11][C:12]1[C:13]([CH3:17])=[N:14][NH:15][CH:16]=1>>[Br:11][C:12]1[C:13]([CH3:17])=[N:14][N:15]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][CH:9]=[CH:10][C:3]=23)[CH:16]=1

Participants

3

Reactant 2

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 178434489HCID 178434489, compound

Product 1

HCID 177544654-(4-bromo-3-methyl-1H-pyrazol-1-yl)-1H-pyrrolo[2,3-b]pyridineYield 87.5%

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.00033 mol) and 4-bromo-3-methyl-1H-pyrazole (0.10 g, 0.00066 mol) was heated at 130° C. overnight. The reaction mixture then was subjected to column chromatography (eluting with 5% MeOH/DCM, 0.5% NH4OH, on silica gel) to give 80 mg pale yellow solid which was triturated with MeOH (1.5 mL) to yield the product as a pale yellow solid (44 mg, 44% yield).

Workup

  1. washThe reaction mixture then was subjected to column chromatography (eluting with 5% MeOH/DCM, 0.5% NH4OH, on silica gel)

Sources & evidence

ORD record
ord-0655278322ac48cd8d34c7d13d48d0cc
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Linked notes

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