4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 4-[4-(3,5-Dimethyl-1H-pyrazol-4-yl)-phenyl]-4-phenyl-piperidine

HRID 2361775Notes

Reaction equation

HRID 2361775 reaction equation
CC1(C)C(C)(C)OB(C2C=NNC=2)O1.Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.[CH3:34][C:35]1[C:39](B2OC(C)(C)C(C)(C)O2)=[C:38]([CH3:49])[NH:37][N:36]=1>>[CH3:34][C:35]1[C:39]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[C:38]([CH3:49])[NH:37][N:36]=1

Participants

4

Reactant 3

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 3871102HCID 3871102, compoundHCID 162177133,5-Dimethylpyrazole-4-boronic acid, pinacol ester

Product 1

HCID 112560094-[4-(3,5-Dimethyl-1H-pyrazol-4-yl)-phenyl]-4-phenyl-piperidine

Procedure

By following the procedure described in Example 1 but substituting 2-(4-chlorophenyl)-2-phenylethylamine hydrochloride and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 4-(4-chloro-phenyl)-4-phenyl-piperidine and 3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole, the title compound was obtained. LC/MS: (PS-A2) Rt 2.95 [M+H]+ 315. 1H NMR (Me-d3-OD) δ 2.22 (6H, s), 2.66-2.76 (4H, m), 3.16-3.28 (4H, m), 7.19-7.44 (9H, m).

Sources & evidence

ORD record
ord-562118ae213d4a25b0baa47868a244d3
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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