Trimethyl borate → (1-(3-chloro-2-methylbenzyl)-2-(difluoromethyl)-6-morpholino-1H-benzo[d]imidazol-4-yl)boronic acid
Reaction equation
Br[C:2]1[C:10]2[N:9]=[C:8]([CH:11]([F:13])[F:12])[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=3[CH3:22])[C:6]=2[CH:5]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:3]=1.C[O:30][B:31](OC)[O:32]C>>[Cl:21][C:17]1[C:16]([CH3:22])=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:7]1[C:6]2[CH:5]=[C:4]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:3]=[C:2]([B:31]([OH:32])[OH:30])[C:10]=2[N:9]=[C:8]1[CH:11]([F:13])[F:12]Participants
3
Procedure
The titled compound was prepared from 4-(4-bromo-1-(3-chloro-2-methylbenzyl)-2-(difluoromethyl)-1H-benzo[d]imidazol-6-yl)morpholine (430 mg, 0.913 mmol) using Method A with trimethylborate to give the product (55 mg, 0.126 mmol, 13.82% yield) as a light brown solid. LC/MS: MS (ES+) m/e 436.2 [M+H]+; 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.44-7.58 (m, 1H), 7.27-7.38 (m, 1H), 7.15 (d, J=2.27 Hz, 1H), 7.00 (t, J=7.96 Hz, 1H), 6.26 (d, J=7.58 Hz, 1H), 5.75 (s, 2H), 3.81-3.94 (m, 4H), 2.50 (s, 3H)
Sources & evidence
- ORD record
- ord-85b01bd920d6486cbe52b27387b477b5
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778937B2
Reaction notes
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