4-Bromo-1H-pyrrolo[2,3-b]pyridine → HCID 68907339, compound

HRID 1962722Notes

Reaction equation

HRID 1962722 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]([F:17])([F:16])[C:13]([OH:15])=[O:14].[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>>[F:11][C:12]([F:17])([F:16])[C:13]([OH:15])=[O:14].[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 68907339HCID 68907339, compound

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-c12a416758934220964b61137b1d5ea6
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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