Trimethyl borate → HCID 71599461, compound

HRID 1622458Notes

Reaction equation

Br[C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[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:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][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]=[C:8]1[CH3:11]

Participants

Reactant 2

HCID 8470Trimethyl borate

HCID 86687822HCID 86687822, compound

Product 1

HCID 71599461HCID 71599461, compound

Procedure

The titled compound was prepared from 4-(4-bromo-1-(3-chlorobenzyl)-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine (0.65 g, 1.545 mmol) using Method A with trimethylborate to give the product (109 mg, 17%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.82 (s, 3H) 3.22 (m, 4H) 3.78 (m, 4H) 5.69 (s, 2H) 7.19 (m, 1H) 7.33-7.48 (m, 4H) 7.78 (s, 1H); MS (ES+) 386.0 m/z.

Sources & evidence

ORD record: ord-d035b2565094473383587fd548242041
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778937B2

Reaction notes

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