B-[3-(2-Methylpropoxy)phenyl]boronic acid → 3-Chloro-5-fluoro-3'-isobutoxybiphenyl-4-amine

HRID 2360420Notes

Reaction equation

HRID 2360420 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=1.[CH2:11]([O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)[CH:12]([CH3:14])[CH3:13]>>[Cl:10][C:4]1[CH:3]=[C:2]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:15][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:21]=2)[CH:8]=[C:7]([F:9])[C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 16217826B-[3-(2-Methylpropoxy)phenyl]boronic acidHCID 204346204-Bromo-2-chloro-6-fluoroaniline

Product 1

HCID 669973413-Chloro-5-fluoro-3'-isobutoxybiphenyl-4-amineYield 68.8%

Procedure

The title compound (0.180 g) was prepared from 4-bromo-2-chloro-6-fluoroaniline (0.2 g, 0.89 mmol) and 3-isobutoxyphenylboronic acid (0.224 g, 1.16 mmol) as a yellow solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.44-7.41 (m, 2H), 7.27 (t, J 7.9, 1H), 7.17-7.10 (m, 2H), 6.84-6.81 (m, 1H), 5.50 (s, 2H), 3.83 (d, J 6.5, 2H), 2.07-1.97 (m, 1H), 1.00 (d, J 6.7, 6H).

Sources & evidence

ORD record
ord-1a6acda61dfe48ef842307673034f270
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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