Dichloromethane → (5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2,6-dichloro-3-fluorophenyl)acetonitrile

HRID 2095737Notes

Reaction equation

HRID 2095737 reaction equation
C[Si]([C:5]#[N:6])(C)C.[Br-].[In+3].[Br-].[Br-].C(Cl)Cl.[Br:14][C:15]1[CH:16]=[C:17]2[C:23]([CH:24]([C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[C:28]([F:33])[C:27]=3[Cl:34])O)=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1>>[Br:14][C:15]1[CH:16]=[C:17]2[C:23]([CH:24]([C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[C:28]([F:33])[C:27]=3[Cl:34])[C:5]#[N:6])=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 82115Trimethylsilyl cyanideHCID 167051indium(III)bromideHCID 67004517(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2,6-dichloro-3-fluorophenyl)methanol

Product 1

HCID 67004878(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2,6-dichloro-3-fluorophenyl)acetonitrile

Procedure

To a stirred mixture of trimethylsilyl cyanide (0.51 mL, 3.8 mmol) and indium(III) bromide (34.1 mg, 0.0961 mmol) in DCM (5.00 mL, 78.0 mmol) was added (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2,6-dichloro-3-fluorophenyl)methanol (150.0 mg, 0.3846 mmol). The resulting mixture was stirred at rt overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (DCM/Hexane 1:1 as eluent). 1H NMR (400 MHz, CD3OD): δ=6.52 (s, 1H), 7.39 (d, J=1.0 Hz, 1H), 7.45 (t, J=8.7 Hz, 1H), 7.63 (dd, J=9.1, 4.8 Hz, 1H), 8.02 (d, J=2.0 Hz, 1H), 8.31 (d, J=2.3 Hz, 1H). MS (ES+): m/z 397.85, 399.88, 401.85 [MH+]. HPLC: tR=4.19 min (OpenLynx, polar—5 min).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography (DCM/Hexane 1:1 as eluent)
  3. customHPLC: tR=4.19 min (OpenLynx, polar—5 min)

Sources & evidence

ORD record
ord-c83e26a9d4ee4745b1de513a071b1277
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

Loading…