Potassium Phosphate, Tribasic → [5-(3'-chloro-biphenyl-3-yl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone

HRID 1011911Notes

Reaction equation

HRID 1011911 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[C:12]([C:16]2[N:20]([CH3:21])[N:19]=[C:18]([C:22]([N:24]3[CH2:28][CH2:27][CH:26]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:25]3)=[O:23])[C:17]=2[CH3:34])[CH:13]=[CH:14][CH:15]=1.[Cl:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1>>[Cl:35][C:36]1[CH:41]=[C:40]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[N:20]([CH3:21])[N:19]=[C:18]([C:22]([N:24]4[CH2:28][CH2:27][CH:26]([N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])[CH2:25]4)=[O:23])[C:17]=3[CH3:34])[CH:11]=2)[CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734323(3-Chlorophenyl)boronic acidHCID 67315151[5-(3-bromo-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone

Product 1

HCID 57555079[5-(3'-chloro-biphenyl-3-yl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanoneYield 56%

Procedure

In analogy to the procedure described in example 14C] but with 2.8 eq of K3PO4, [5-(3-bromo-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone and 3-chlorophenylboronic acid gave [5-(3′-chloro-biphenyl-3-yl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone in 56% yield as light brown oil. MS: 451.0 (MH+, 1 Cl).

Sources & evidence

ORD record
ord-dcc16ab01da64c0fb77ba2e10259659e
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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