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

HRID 40928Notes

Reaction equation

HRID 40928 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.FC(F)(F)C(O)=O.[NH:18]1[CH:22]=[C:21]([C:23]2[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=2)[C:26]#[N:27])[CH:20]=[N:19]1>>[NH:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([N:18]3[CH:22]=[C:21]([C:23]4[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=4)[C:26]#[N:27])[CH:20]=[N:19]3)=[C:3]2[CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 665974043-(1H-pyrazol-4-yl)benzonitrile trifluoroacetate

Product 1

HCID 574776653-[1-(1H-Pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl]benzonitrile

Conditions

Temperature
180 °C

Procedure

A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (25.0 mg, 0.000127 mol) and 3-(1H-pyrazol-4-yl)benzonitrile trifluoroacetate (23.6 mg, 0.0000833 mol) was heated at 180° C., neat overnight. The crude residue was purified by HPLC on a C-18 column eluting with a water; ACN gradient containing 0.2% TFA to give the title compound as an amorphous white solid, LC/MS (M+H)+: 286, 1H NMR (DMSO-d6) δ 11.85 (bs, 1H), 9.18(s, 1H), 8.42(s, 1H), 8.28(s, 1H), 8.25(d, 1H, J=5.0), 8.07(d, 1H, J=7.0), 7.64(d, 1H, J=7.0), 7.56(t, 1H, J=7.0), 7.51(m, 1H), 7.47(d, 1H, J=5.0), 7.03(m,1H).

Workup

  1. customThe crude residue was purified by HPLC on a C-18 column
  2. washeluting with a water
  3. additionACN gradient containing 0.2% TFA

Sources & evidence

ORD record
ord-13de056aa4af4d6ba0b43915f327c812
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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