3-Fluorobenzoyl chloride → HCID 89443345, compound

HRID 1771130Notes

Reaction equation

HRID 1771130 reaction equation
[NH2:1][C:2]1[C:3]([F:21])=[C:4]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C(Cl)Cl>[F:21][C:3]1[C:4]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:1][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([F:22])[CH:24]=1

Participants

4

Reactant 2

HCID 743763-Fluorobenzoyl chlorideHCID 89462331HCID 89462331, compound

Product 1

HCID 89443345HCID 89443345, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-2,6-difluorophenyl)(quinoxalin-6-yl)methanone (40 mg, 0.14 mmol, 1.0 eq.) in DCM (5 mL) were added TEA (31 mg, 0.28 mmol, 2.0 eq.) and 3-fluorobenzoyl chloride (22 mg, 0.14 mmol, 1.0 eq.). The resulting mixture was stirred at rt for 1 h, then concentrated. The residue was purified via flash column chromatography (PE/EA=2/1, v/v) to afford N-(2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl)-3-fluorobenzamide (26 mg, 45%). LRMS (M−H+) m/z calculated 406.1. found 406.1. 1H NMR (CDCl3, 400 MHz) δ 8.88-8.90 (dd, 2H), 8.55-8.60 (m, 1H), 8.43 (s, 1H), 8.33-8.35 (m, 1H), 8.19-8.21 (m, 1H), 7.88 (s, 1H), 7.54-7.57 (m, 2H), 7.40-7.45 (m, 1H), 7.22-7.24 (m, 1H), 7.04-7.09 (t, 1H).

Workup

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

Sources & evidence

ORD record
ord-122d592fb5c44281b76b78a466a1e41d
Source dataset
uspto-grants-2016_02
Patent number
US09249110B2

Reaction notes

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