Sodium Carbonate → HCID 11317311, compound

HRID 1991371Notes

Reaction equation

Br[C:2]1[C:3]([CH3:29])=[C:4]([C:21]([OH:28])=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:23]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=1[O:16][C:17]([F:20])([F:19])[F:18])=[O:6].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5]([C:4]2[C:3]([CH3:29])=[C:2]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]=2[OH:28])=[O:6])=[C:9]([O:16][C:17]([F:20])([F:19])[F:18])[CH:10]=1)#[N:15]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-Bromo-5-tert-butyl-N-(2-trifluoromethoxy-4-cyano-phenyl)-6-hydroxy-2-methyl-benzamide (0.141 g, 0.3 mmole) in dioxane (5 ml) under nitrogen, phenylboronic acid (37.0 mg, 0.3 mmole), tetrakis(triphenylphosphine)palladium(0) (7 mg, 0.006 mmole) and sodiumcarbonate (1.05 ml, 2 M solution in water) were added. The reaction mixture was heated at 100° C. for 48 hours. The reaction mixture was evaporated, diluted with ethyl acetate and the organic phase was washed with citric acid solution (10%). The organic phase was dried over sodium sulphate and evaporated. The crude compound was purified by column chromatography.

Workup

customThe reaction mixture was evaporated
additiondiluted with ethyl acetate
washthe organic phase was washed with citric acid solution (10%)
dry with materialThe organic phase was dried over sodium sulphate
customevaporated
customThe crude compound was purified by column chromatography

Sources & evidence

ORD record: ord-5c95c94d86fd444493748b27e1f33e08
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645791B2

Reaction notes

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