4-AMINO-3-FLUOROPHENYLBORONIC ACID → HCID 58362372, compound

HRID 2361519Notes

Reaction equation

HRID 2361519 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.[NH2:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][C:17]=1[F:25]>>[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:19]1[CH:20]=[CH:21][C:16]([NH2:15])=[C:17]([F:25])[CH:18]=1

Participants

3

Reactant 2

HCID 101925824-AMINO-3-FLUOROPHENYLBORONIC ACIDHCID 58362356HCID 58362356, compound

Product 1

HCID 58362372HCID 58362372, compound

Procedure

The title compound was synthesized using General Experimental Procedure A (Suzuki coupling reaction) from 2-bromobenzo[4,5]imidazo[1,2-a]pyrimidine and (4-amino-3-fluorophenyl)boronic acid on a 0.059 mmol scale. 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-2-fluoroaniline was obtained as a orange solid (10 mg, 61%). 1H NMR (400 MHz, DMSO-d6): δ 9.63 (d, J=7.2 Hz, 1H), 8.45 (d, J=8.0 Hz, 1H), 8.20 (d, J=7.2 Hz, 1H), 8.12 (dd, J=23.2, 2.0 Hz, 1H), 8.11 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.72 (t, J=7.2 Hz, 1H), 7.62 (d, J=7.6 Hz, 1H), 6.94 (t, J=8.8 Hz, 1H); MS (ESI) m/z [M+H]+279.

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-0868efec2ec54002b8bf99a2689251c5
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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