3-Fluorophenylboronic acid → HCID 86670332, compound

HRID 1972440Notes

Reaction equation

HRID 1972440 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:13]=[C:14]([C:32]([OH:41])([C:37]([F:40])([F:39])[F:38])[C:33]([F:36])([F:35])[F:34])[CH:15]=[CH:16][C:17]=1[N:18]1[CH2:23][CH2:22][N:21]([S:24]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)(=[O:26])=[O:25])[CH2:20][CH2:19]1>>[F:40][C:37]([F:38])([F:39])[C:32]([C:14]1[CH:15]=[C:16]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:17]([N:18]2[CH2:23][CH2:22][N:21]([S:24]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)(=[O:25])=[O:26])[CH2:20][CH2:19]2)=[CH:12][CH:13]=1)([OH:41])[C:33]([F:36])([F:35])[F:34]

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 86670331HCID 86670331, compound

Product 1

HCID 86670332HCID 86670332, compound

Procedure

Following the procedure outlined for Example 69, 3-fluorophenylboronic acid (20.23 mg, 0.145 mmol) 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′-fluoro-6-(4-(2-thiophenylsulfonyl)-1-piperazinyl)-3-biphenylyl)-2-propanol. 1H NMR (300 MHz, CD3OD) δ 7.89 (d, J=4.2 Hz, 1H), 7.66 (s, 1H), 7.58 (d, J=2.6 Hz, 1H), 7.53 (s, 1H), 7.42-7.31 (m, 1H), 7.27 (d, J=4.0 Hz, 3H), 7.17 (d, J=8.6 Hz, 1H), 7.09-6.97 (m, 1H), 2.96 (br. s, 8H). m/z (ESI, +ve ion) 568.8 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=3.67 μM; GK-GKRP EC50 (LC MS/MS)=1.84 μM.

Sources & evidence

ORD record
ord-70efc41d701b43c0831cd66039fb4e15
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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