Benzyl Bromide → HCID 71515486, compound

HRID 1771150Notes

Reaction equation

HRID 1771150 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][CH:16]=[N:15]2)=[O:11].C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC#N>[CH2:29]([O:8][C:7]1[C:2]([F:1])=[C:3]([C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[N:15]3)=[O:11])[C:4]([F:9])=[CH:5][CH:6]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 71547769HCID 71547769, compound

Product 1

HCID 71515486HCID 71515486, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2,6-difluoro-3-hydroxyphenyl)(quinoxalin-6-yl)methanone (57 mg, 0.2 mmol, 1.0 eq.) in CH3CN (10 mL) were added K2CO3 (56 mg, 0.4 mmol, 2 eq.) and (bromomethyl)benzene (38 mg, 0.22 mmol, 1.1 eq). The resulting mixture was stirred at rt overnight, then concentrated. The residue was purified via flash column chromatography (PE/EA=10/1, v/v) to afford (3-(benzyloxy)-2,6-difluorophenyl)(quinoxalin-6-yl)methanone as brown solid (38.4 mg, 51.2%). LRMS (M+H+) m/z calculated 377.1, found 377.1. 1H NMR (CDCl3, 400 MHz) δ 8.93-8.95 (d, 2 H), 8.48 (s, 1 H), 8.39-8.41 (d, 1 H), 8.23-8.26 (d, 1 H), 7.33-7.45 (m, 5 H), 7.10-7.16 (m, 1 H), 6.91-6.95 (t, 1 H), 5.17 (s, 2 H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via flash column chromatography (PE/EA=10/1

Sources & evidence

ORD record
ord-c884d6dec16540eeb67c8d1f7188c059
Source dataset
uspto-grants-2016_02
Patent number
US09249111B2

Reaction notes

Loading…