4-AMINO-3-FLUOROPHENYLBORONIC ACID → HCID 58362355, compound

HRID 2361520Notes

Reaction equation

HRID 2361520 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]([NH:15][CH2:21][CH2:16][CH2:17][F:25])=[C:17]([F:25])[CH:18]=1

Participants

3

Reactant 2

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

Product 1

HCID 58362355HCID 58362355, compound

Procedure

The title compound was prepared first 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 and then using General Experimental Procedure S for alkylation. 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-2-fluoro-N-(3-fluoropropyl)aniline was obtained as a orange solid. 1H NMR (400 MHz, methanol-d4): δ 9.12 (d, J=7.6, 1H), 8.06 (d, J=8.0 Hz, 1H), 8.04-7.98 (m, 2H), 7.76 (d, J=8.0 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.52 (t, J=8.0 Hz, 1H), 7.38 (t, J=7.6 Hz, 1H), 6.86 (t, J=8.4 Hz, 1H), 4.62 (t, J=5.6 Hz, 1H), 4.50 (t, J=5.6 Hz, 1H), 3.41 (t, J=6.8 Hz, 1H), 2.03 (m, 2H); MS (ESI) m/z [M+H]+339.

Workup

  1. customThe title compound was prepared first

Sources & evidence

ORD record
ord-07531382c8d04544a26c220d3bd04e3e
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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