(4-Cyano-3-fluorophenyl)boronic acid → HCID 53339261, compound

HRID 2361512Notes

Reaction equation

HRID 2361512 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=[C:4]2[N:3]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][C:18]=1[F:26])#[N:16]>>[N:3]1[C:4]2[N:5]([C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH:6]=[CH:7][C:2]=1[C:21]1[CH:20]=[CH:19][C:18]([F:26])=[C:17]([CH:22]=1)[C:15]#[N:16].[N:3]1[C:4]2[N:5]([C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH:6]=[CH:7][C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[C:18]([F:26])[CH:19]=1

Participants

4

Reactant 2

HCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 58362356HCID 58362356, compound

Product 2

HCID 53339261HCID 53339261, compoundYield 41%HCID 58362577HCID 58362577, compound

Procedure

The title compound was prepared using General Experimental Procedure A (Suzuki coupling reaction) from 2-bromobenzo[4,5]imidazo[1,2-a]pyrimidine and (4-cyano-3-fluorophenyl)boronic acid on a 0.1 mmol scale. The residue was washed with water (3×5 mL), EtOAc (3×2 mL), and DCM (3×2 mL) and dried under high vacuum to afford 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-2-fluorobenzonitrile (T747) as a orange solid (12 mg, 41%). 1H NMR (400 MHz, DMSO-d6): δ 9.67 (d, J=7.2 Hz, 1H), 8.86 (dd, J=5.6, 2.0 Hz, 1H), 8.74 (m, 1H), 8.33 (d, J=7.6 Hz, 1H), 7.91 (d, J=7.2 Hz, 1H), 7.84 (d, J=9.2 Hz, 1H), 7.760 (t, J=8.8 Hz, 1H), 7.54 (t, J=7.2 Hz, 1H), 7.42 (t, J=7.6 Hz, 1H); MS (ESI) m/z [M+H]+289.

Workup

  1. washThe residue was washed with water (3×5 mL), EtOAc (3×2 mL), and DCM (3×2 mL)
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-6e0aa9e2140c45768f5e7cf208f98dc5
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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