(4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acid → (4R,5R)-5-[4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]-4-methyl-1,3-oxazolidin-2-one

HRID 1028562Notes

Reaction equation

HRID 1028562 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C@H:12]1[O:16][C:15](=[O:17])[NH:14][C@@H:13]1[CH3:18].[F:19][C:20]1[C:25]([CH:26]([CH3:28])[CH3:27])=[CH:24][C:23](B(O)O)=[C:22]([O:32][CH3:33])[CH:21]=1>>[F:19][C:20]1[C:25]([CH:26]([CH3:28])[CH3:27])=[CH:24][C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[C@H:12]2[O:16][C:15](=[O:17])[NH:14][C@@H:13]2[CH3:18])=[C:22]([O:32][CH3:33])[CH:21]=1

Participants

3

Reactant 2

HCID 53363739(4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acidHCID 59726151(4R,5R)-5-[2-iodo-5-(trifluoromethyl)phenyl]4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 59135143(4R,5R)-5-[4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]-4-methyl-1,3-oxazolidin-2-one

Procedure

Following the procedure described in EXAMPLE 81, 240 mg of (4R,5R)-5-[2-iodo-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one and 171 mg of (4-fluoro-5-isopropyl-2-methoxyphenyl)boronic acid (EXAMPLE 78) gave the title compound. Mass spectrum (ESI) 412.3 (M+1). 1H NMR signals are doubled because of atropoisomerism. 1H NMR (500 MHz, CDCl3): δ 7.79, 7.77 (s, 1H), 7.64, 7.62 (dd, J˜2.5 Hz, 8 Hz, 1H), 7.32, 7.31 (d, J˜8 Hz, 1H), 7.00, 6.95 (d, J=8.5 Hz, 1H), 6.70, 6.67 (d, J=12 Hz, 1H), 6.47, 6.43 (s, 1H), 5.08, 5.04 (d, J=5 Hz, 0.1H), 3.68-3.80 (m, 3.5H), 3.53 (m, 0.5H), 3.21 (m, 1H), 1.19-1.30 (m, 6H), 0.95, 0.77 (d, J=6 Hz, 3H).

Sources & evidence

ORD record
ord-180df30be8074a5cae3f1233ca4f6ea2
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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