2-Fluoro-5-methoxyphenylboronic acid → 3-[3-(2'-Fluoro-5'-methoxy-2-trifluoromethoxy-biphenyl-4-ylmethoxy)-phenyl]-propionic acid

HRID 1662347Notes

Reaction equation

HRID 1662347 reaction equation
Cl[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[O:21][C:22]([F:25])([F:24])[F:23].[F:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1B(O)O>>[F:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[O:21][C:22]([F:25])([F:24])[F:23]

Participants

3

Reactant 2

HCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 577060113-(3-(4-Chloro-3-(trifluoromethoxy)benzyloxy)phenyl)-propanoic acid

Product 1

HCID 577061773-[3-(2'-Fluoro-5'-methoxy-2-trifluoromethoxy-biphenyl-4-ylmethoxy)-phenyl]-propionic acid

Procedure

Compound 38 was synthesized using the procedure described above for preparing 13.3 using compound 37.3 and 2-fluoro-5-methoxyphenylboronic acid 38.1 (available from Aldrich). MS ESI (neg.) m/e: 463 (M−H). 1H NMR (400 MHz, CD3CN) δ ppm 7.47-7.54 (3H, m), 7.22 (1H, t, J=7.8 Hz), 7.12-7.17 (1H, m), 6.98 (1H, dt, J=9.0, 3.5 Hz), 6.90-6.93 (2H, m), 6.85 (2H, dd, J=8.0, 2.2 Hz), 5.16 (2H, s), 3.79 (3H, s), 2.86 (2H, s), 2.56-2.62 (2H, m).

Sources & evidence

ORD record
ord-ec0a0fb1b04940a59ac791651255e21f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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