Sodium Bicarbonate → HCID 66579429, compound

HRID 1183263Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH2:18][CH2:17]2)=[O:15])=[CH:4][CH:3]=1.[CH2:29]([O:31][C:32]([C:34]1([C:37]2[CH:42]=[CH:41][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:39][CH:38]=2)[CH2:36][CH2:35]1)=[O:33])[CH3:30].C(=O)(O)[O-].[Na+]>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.COCCOC>[CH2:29]([O:31][C:32]([C:34]1([C:37]2[CH:38]=[CH:39][C:40]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4[O:12][N:11]=[C:10]([CH3:13])[C:9]=4[C:14]([N:16]4[CH2:21][CH2:20][N:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=5[CH3:28])[CH2:18][CH2:17]4)=[O:15])=[CH:6][CH:7]=3)=[CH:41][CH:42]=2)[CH2:35][CH2:36]1)=[O:33])[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-(4-o-tolyl-piperazin-1-yl)-methanone (0.156 g, 0.36 mmol), 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester (0.168 g, 0.53 mmol), tetrakis(triphenylphosphine)palladium(0) (0.042 g, 0.04 mmol), and sodium bicarbonate (0.076 g, 0.90 mmol) were combined in 3:1 DME:H2O, and the mixture was purged with N2 (g). The reaction was stirred at 80° C. for 1 hour and then cooled and concentrated. The crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound.

Workup

customH2O, and the mixture was purged with N2 (g)
temperaturecooled
concentrationconcentrated
customThe crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-4b710736771b4d838da26f6c7be164de
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664220B2

Reaction notes

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