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

HRID 1622466Notes

Reaction equation

HRID 1622466 reaction equation
Br[C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=3[CH3:19])[C:6]=2[CH:5]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:3]=1.C[O:27][B:28](OC)[O:29]C>>[Cl:18][C:14]1[C:13]([CH3:19])=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][N:7]1[C:6]2[CH:5]=[C:4]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:3]=[C:2]([B:28]([OH:29])[OH:27])[C:10]=2[N:9]=[CH:8]1

Participants

3

Reactant 2

HCID 8470Trimethyl borateHCID 866878284-(4-bromo-1-(3-chloro-2-methylbenzyl)-1H-benzo[d]imidazol-6-yl)morpholine

Product 1

HCID 71599462(1-(3-chloro-2-methylbenzyl)-6-morpholino-1H-benzo[d]imidazol-4-yl)boronic acid

Procedure

The titled compound was prepared from 4-(4-bromo-1-(3-chloro-2-methylbenzyl)-1H-benzo[d]imidazol-6-yl)morpholine (400 mg, 0.951 mmol) using Method A with trimethylborate to give the product (23 mg, 6%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.41 (s, 3H) 3.12-3.18 (m, 4H) 3.82-3.90 (m, 4H) 5.61 (s, 2H) 6.89 (d, J=7.07 Hz, 2H) 7.17 (t, J=7.83 Hz, 1H) 7.27 (d, J=2.27 Hz, 1H) 7.42 (d, J=8.08 Hz, 1H) 8.39 (s, 1H); LC/MS: MS (ES+) m/e 386 [M+H]+.

Sources & evidence

ORD record
ord-0fd6d50ef61d4592a90b61685660a91c
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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