4-Bromo-2,6-difluoroaniline → HCID 66997151, compound

HRID 2360446Notes

Reaction equation

HRID 2360446 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[CH3:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18](B3OC(C)(C)C(C)(C)O3)[CH:19]=2)[NH:14][CH:13]=1>>[F:9][C:7]1[CH:8]=[C:2]([C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH3:11])[CH:3]=[C:4]([F:10])[C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 6101914-Bromo-2,6-difluoroanilineHCID 210726073-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 66997151HCID 66997151, compoundYield 54.9%

Procedure

The title compound (68 mg) was prepared from 4-bromo-2,6-difluoroaniline (100 mg, 0.48 mmol) and 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (160 mg, 0.62 mmol) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.71 (s, 1H), 7.67 (s, 1H), 7.33-7.29 (m, 2H), 7.28-7.21 (m, 2H), 7.09 (s, 1H), 5.12 (s, 2H), 2.27 (s, 3H).

Sources & evidence

ORD record
ord-f8dbece762574bd2b98c8b807c975a69
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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