(3-Methyl-1-trityl-1H-pyrazol-4-yl)boronic acid → 4-(4-Chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine

HRID 924752Notes

Reaction equation

HRID 924752 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:22][C:23]1[C:27](B(O)O)=[CH:26][N:25]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:24]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:9]2([C:6]3[CH:7]=[CH:8][C:3]([C:27]4[C:23]([CH3:22])=[N:24][N:25]([C:31]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)([C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)[C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[CH:26]=4)=[CH:4][CH:5]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 22031628(3-Methyl-1-trityl-1H-pyrazol-4-yl)boronic acidHCID 672352524-(4-Bromophenyl)-4-(4-chlorophenyl)piperidine--hydrogen chloride (1/1)

Product 1

HCID 672351344-(4-Chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

4-(4-bromo-phenyl)-4-(4-chloro-phenyl)-piperidine hydrochloride was reacted with 3-methyl-1-trityl-1H-pyrazole-4-boronic acid* following the procedure set out in Example 1, but using tetrakis(triphenylphosphine) palladium (0) as the catalyst to give the title compound. LC/MS: (PS-B3) Rt 2.78 min [M+H]+ 594. * This starting material can be made by the method described in EP1382603

Sources & evidence

ORD record
ord-5f3990304ebf45b5935fba52f06c083a
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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