4-Bromo-1H-pyrrolo[2,3-b]pyridine → 4-Fluoro-2-[1-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenol

HRID 40921Notes

Reaction equation

HRID 40921 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]2[CH:23]=[CH:22][NH:21][N:20]=2)[CH:13]=1>>[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]2[CH:23]=[CH:22][N:21]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[NH:8][CH:9]=[CH:10][C:3]=34)[N:20]=2)[CH:13]=1

Participants

3

Reactant 2

HCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 178516117HCID 178516117, compound

Product 1

HCID 1359272004-Fluoro-2-[1-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenol

Procedure

4-Bromo-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.00025 mol) and 4-fluoro-2-(1H-pyrazol-3-yl)phenol (0.150 g, 0.000842 mol) were heated neat to 160° C. for 5 h. The reaction was allowed to cool to rt and the residue was purified by prep LC-MS on a C-18 column eluting with a water/ACN gradient containing 0.2% TFA to give the title compound, (0.052 g, 20%, as an amorphous white solid, LC/MS (M+H)+295, 1H NMR (DMSO-d6) δ 12.01 (bs, 1H), 10.25(bs, 1H), 8.81(s,1H), 8.35(d, 1H, J=5.5), 7.77(d, 1H, J=9.5), 7.64(m, 1H), 7.59(d, 1H, J=5.5), 7.32(s, 1H), 7.09(m, 1H), 7.05(m, 1H), 7.01(m, 1H).

Workup

  1. customthe residue was purified by prep LC-MS on a C-18 column
  2. washeluting with a water/ACN gradient
  3. additioncontaining 0.2% TFA

Sources & evidence

ORD record
ord-2cbb456fe74f476cae1aed6b1cfa97ec
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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