(R)-4-bromo-alpha-methylbenzylamine → (R)-1-(2'-methoxy-5'-methyl-biphenyl-4-yl)-ethylamine

HRID 2422838Notes

Reaction equation

HRID 2422838 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:28][CH2:29]C)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]([NH:16]S(C3C(C)=NN(C)C=3Cl)(=O)=O)[CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.[CH3:31]OC1C=CC(C)=CC=1B(O)O.BrC1C=CC([C@H](N)C)=CC=1>>[CH3:29][O:28][C:5]1[CH:4]=[CH:3][C:2]([CH3:31])=[CH:7][C:6]=1[C:8]1[CH:9]=[CH:10][C:11]([C@H:14]([NH2:16])[CH3:15])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 853000(R)-4-bromo-alpha-methylbenzylamineHCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 16202171(r)-5-Chloro-1,3-dimethyl-1h-pyrazole-4-sulfonic acid [1-(5'-chloro-2'-ethoxy-biphenyl-4-yl)-ethyl]-amide

Product 1

HCID 67245267(R)-1-(2'-methoxy-5'-methyl-biphenyl-4-yl)-ethylamine

Procedure

Prepared in a similar manner to (R)-5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonic acid [1-(5′-chloro-2′-ethoxy-biphenyl-4-yl)-ethyl]-amide (Example 1) using 2-methoxy-5-methylphenylboronic acid and (R)-1-(4-bromophenyl)ethylamine to give (R)-1-(2′-methoxy-5′-methyl-biphenyl-4-yl)-ethylamine which was then reacted with 5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride. Title compound: 1H NMR (400 MHz, DMSO-d6): δ 8.25 (d, 1H), 7.27 (d, 2H), 7.20 (d, 2H), 7.12 (d, 1H), 7.02 (s, 1H), 6.97 (d, 1H), 4.35 (q, 1H), 3.72 (s, 3H), 3.55 (s, 3H), 2.28 (s, 3H), 2.20 (s, 3H), 1.33 (d, 3H) ppm; MS (ESI) m/z: value [M+H]+.

Sources & evidence

ORD record
ord-b1dc404791f74043854bffcfd2f93810
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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