Trimethyl borate → (1-(3-chloro-2-methylbenzyl)-2-(fluoromethyl)-6-morpholino-1H-benzo[d]imidazol-4-yl)boronic acid

HRID 1622474Notes

Reaction equation

HRID 1622474 reaction equation
Br[C:2]1[C:10]2[N:9]=[C:8]([CH2:11][F:12])[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=3[CH3:21])[C:6]=2[CH:5]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:3]=1.C[O:29][B:30](OC)[O:31]C>O>[Cl:20][C:16]1[C:15]([CH3:21])=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:7]1[C:6]2[CH:5]=[C:4]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[CH:3]=[C:2]([B:30]([OH:31])[OH:29])[C:10]=2[N:9]=[C:8]1[CH2:11][F:12]

Participants

4

Reactant 2

HCID 8470Trimethyl borateHCID 866878354-(4-bromo-1-(3-chloro-2-methylbenzyl)-2-(fluoromethyl)-1H-benzo[d]imidazol-6-yl)morpholine

Product 1

HCID 71599463(1-(3-chloro-2-methylbenzyl)-2-(fluoromethyl)-6-morpholino-1H-benzo[d]imidazol-4-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The titled compound was prepared from 4-(4-bromo-1-(3-chloro-2-methylbenzyl)-2-(fluoromethyl)-1H-benzo[d]imidazol-6-yl)morpholine (300 mg, 0.663 mmol) using Method A with trimethylborate to give the product (9.1 mg, 0.020 mmol, 3.09% yield) after lyophilization from water. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.53 (s, 3H) 3.20 (d, J=4.80 Hz, 4H) 3.81-3.86 (m, 4H) 5.75 (s, 1H) 5.83 (s, 2H) 5.86-5.90 (m, 1H) 6.44-6.49 (m, 1H) 6.99-7.03 (m, 1H) 7.09 (s, 1H) 7.39 (s, 1H) 7.58 (s, 1H); LC/MS: MS (ES+) m/e 418 [M+H]+.

Sources & evidence

ORD record
ord-17daf5ddeeda4837a1d203d355186a98
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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