(3-Methoxyphenyl)boronic acid → HCID 56932323, compound

HRID 1972439Notes

Reaction equation

HRID 1972439 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[C:15]([C:33]([OH:42])([C:38]([F:41])([F:40])[F:39])[C:34]([F:37])([F:36])[F:35])[CH:16]=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][N:22]([S:25]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)(=[O:27])=[O:26])[CH2:21][CH2:20]1>>[F:41][C:38]([F:39])([F:40])[C:33]([C:15]1[CH:16]=[C:17]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:18]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)(=[O:26])=[O:27])[CH2:21][CH2:20]2)=[CH:13][CH:14]=1)([OH:42])[C:34]([F:37])([F:36])[F:35]

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 86670331HCID 86670331, compound

Product 1

HCID 56932323HCID 56932323, compound

Procedure

Following the procedure outlined for Example 69, 3-methoxyphenylboronic acid (26.4 mg, 0.173 mmol, Aldrich, St. Louis, Mo.) was coupled to 2-(3-bromo-4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol to afford 1,1,1,3,3,3-hexafluoro-2-(3′-methoxy-6-(4-(2-thiophenylsulfonyl)-1-piperazinyl)-3-biphenylyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.91 (dd, J=4.9, 1.2 Hz, 1H), 7.61-7.54 (m, 2H), 7.49 (d, J=1.2 Hz, 1H), 7.40 (d, J=8.8 Hz, 2H), 7.28 (dd, J=4.9, 3.9 Hz, 1H), 7.11 (d, J=8.6 Hz, 1H), 6.87 (d, J=8.6 Hz, 2H), 3.81 (s, 3H), 2.95 (br. s, 8H). m/z (ESI, +ve ion) 580.8 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=3.34 μM; GK-GKRP EC50 (LC MS/MS)=1.82 μM.

Sources & evidence

ORD record
ord-907892084b3a4c58b5d0f6dfe1d3624c
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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