3-Pyridinylboronic acid → HCID 86670333, compound

HRID 1972441Notes

Reaction equation

HRID 1972441 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:12]=[C:13]([C:31]([OH:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])[CH:14]=[CH:15][C:16]=1[N:17]1[CH2:22][CH2:21][N:20]([S:23]([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)(=[O:25])=[O:24])[CH2:19][CH2:18]1>>[F:39][C:36]([F:37])([F:38])[C:31]([C:13]1[CH:12]=[CH:11][C:16]([N:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)(=[O:24])=[O:25])[CH2:19][CH2:18]2)=[C:15]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:14]=1)([OH:40])[C:32]([F:35])([F:34])[F:33]

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 86670331HCID 86670331, compound

Product 1

HCID 86670333HCID 86670333, compound

Procedure

Following the procedure outlined for Example 69, 3-pyridineboronic acid (21.33 mg, 0.173 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-(3-pyridinyl)-4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 8.67 (d, J=1.6 Hz, 1H), 8.47 (dd, J=4.9, 1.6 Hz, 1H), 8.02-7.94 (m, 1H), 7.89 (dd, J=5.1, 1.2 Hz, 1H), 7.71 (d, J=9.2 Hz, 1H), 7.60-7.53 (m, 2H), 7.43 (dd, J=7.8, 4.9 Hz, 1H), 7.31-7.22 (m, 2H), 2.97 (s, 8H). m/z (ESI, +ve ion) 551.6 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.775 μM; GK-GKRP EC50 (LC MS/MS)=0.783 μM.

Sources & evidence

ORD record
ord-eb10210109064b9da145190b8310c3bd
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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