Sodium Carbonate → 4-Methyl-5-(1-methyl-1H-pyrazol-4-yl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 2204733Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.C([O-])([O-])=O.[Na+].[Na+].Br[C:23]1[C:24]([CH3:46])=[CH:25][C:26]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:27]([CH:37]=1)[C:28]([NH:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=[O:29]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:46][C:24]1[C:23]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)=[CH:37][C:27]([C:28]([NH:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[O:29])=[C:26]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (86 mg, 0.42 mmol), palladium tetrakis (26.2 mg, 0.02 mmol) and Na2CO3 (0.76 ml, 0.76 mmol) were added to a solution of 5-bromo-4-methyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 6; 150 mg, 0.38 mmol) in 1,2-dimethoxyethane (3 ml). The mixture was heated at 120° C. in a microwave for 1 hour. The solvent was removed in vacuo and the residue purified by MDAP to yield the title compound as a white solid. 73 mg.

Workup

customThe solvent was removed in vacuo
customthe residue purified by MDAP

Sources & evidence

ORD record: ord-303a66239e59493ead013c824539ef47
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365551B2

Reaction notes

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