Trimethyl borate → HCID 71599459, compound

HRID 1622456Notes

Reaction equation

HRID 1622456 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]=[CH:15][C:14]=3[Cl: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:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=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

3

Reactant 2

HCID 8470Trimethyl borateHCID 86687821HCID 86687821, compound

Product 1

HCID 71599459HCID 71599459, compound

Procedure

The titled compound was prepared from 4-(4-bromo-1-(2-chlorobenzyl)-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine (0.2 g, 0.475 mmol) using Method A with trimethylborate to give the product (0.272 g, 39%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.77 (s, 3H) 3.15-3.25 (m, 4H) 3.65-3.82 (m, 4H) 5.75 (s, 2H) 6.82-6.88 (m, 1H) 7.22-7.30 (m, 1H) 7.32-7.40 (m, 2H) 7.56 (dd, J=7.96, 1.14 Hz, 1H) 7.80 (d, J=1.95 Hz, 1H); MS (ES+) 386.0 m/z

Sources & evidence

ORD record
ord-b3e8b1ebb0ea47cab27a824d8c16828a
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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