1,2-Dimethoxyethane → HCID 24967983, compound

HRID 1174558Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[NH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:20]([C:24]1[CH:48]=[CH:47][C:27]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[C:32]=2[CH3:46])=[O:29])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OCC)(=O)C.O>[C:20]([C:24]1[CH:48]=[CH:47][C:27]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:2]3[CH:3]=[C:4]([NH:10][C:11]4[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[NH:13][N:12]=4)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=3)[C:32]=2[CH3:46])=[O:29])=[CH:26][CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 5-Bromo-3-(5-tert-butyl-1H-pyrazol-3-ylamino)-1-methyl-1H-pyridin-2-one (125 mg; 0.38 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (180 mg; 0.46 mmol), tetrakis-(triphenylphosphine)palladium (24 mg; 0.02 mmol), sodium carbonate (400 mg; 1.2 mmol), and 1,2-dimethoxyethane (4 mL) and water (4 mL) were heated in a sealed microwave reactor for 5 min (135° C., 300 W). The mixture diluted with ethyl acetate, adsorbed onto silica gel, and flash chromatographed (9:1 CH2Cl2:MeOH) to give 4-tert-Butyl-N-{3-[5-(5-tert-butyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl]-2-methyl-phenyl}-benzamide as a tan solid (205 mg).

Workup

customchromatographed (9:1 CH2Cl2:MeOH)

Sources & evidence

ORD record: ord-cdc1ddfdf0ff4c9388f8245e183a745d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838523B2

Reaction notes

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