3-(Methoxycarbonyl)benzeneboronic acid → Methyl 4'-(1-(isobutylamino)-2-methyl-1-oxopropan-2-yl)biphenyl-3-carboxylate

HRID 1175573Notes

Reaction equation

HRID 1175573 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)=[O:21]>>[CH2:12]([NH:11][C:9](=[O:10])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([C:20]([O:19][CH3:18])=[O:21])[CH:27]=2)=[CH:3][CH:4]=1)([CH3:17])[CH3:16])[CH:13]([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 687750752-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide

Product 1

HCID 58789412Methyl 4'-(1-(isobutylamino)-2-methyl-1-oxopropan-2-yl)biphenyl-3-carboxylateYield 65%

Procedure

Prepared in a similar manner to Example 8 from 2-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide (Example 1a) and 3-(methoxycarbonyl)phenylboronic acid. Yield: 65%. 1H NMR (400 MHz, CDCl3): δ 0.8 (d, 6H), 1.65 (s, 6H), 1.67-1.70 (m, 1H), 3 (t, 2H), 3.9 (s, 1H), 5.2 (broad, 1H), 7.4-7.56 (m, 3H), 7.6 (d, 2H), 7.8 (d, 1H), 8.1 (dd, 1H), 8.3 (d, 1H). MS (M+H, 354).

Sources & evidence

ORD record
ord-aee968b77b9e4deea3ee9a3d4abaafa6
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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