Water → HCID 90390781, compound

HRID 1048865Notes

Reaction equation

Br[C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:13].[CH3:14][S:15]([NH:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:16].C(=O)([O-])[O-].[Na+].[Na+].O>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>[NH2:6][C:5]1[CH:7]=[C:8]([C:9]([F:12])([F:11])[F:10])[C:2]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:18][S:15]([CH3:14])(=[O:16])=[O:17])[CH:24]=2)=[C:3]([Cl:13])[CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-3-chloro-5-(trifluoromethyl)aniline (573 mg, 2.09 mmol, Eq: 1.00), 3-(methylsulfonamido)phenylboronic acid (529 mg, 2.46 mmol, Eq: 1.18) and tetrakis(triphenylphosphine)palladium (0) (211 mg, 183 μmol, Eq: 0.0875) was degassed (vacuum/nitrogen cycles) then degassed dioxane (6.87 ml) (nitrogen bubbling with sonication) and a degassed (nitrogen bubbling with sonication) 2M solution of sodium carbonate in water (1.83 ml, 3.66 mmol, Eq: 1.75) were added. The mixture was stirred at 100° C. for 18 h. The reaction mixture was adsorbed unto silica (2 g), concentrated and purified on silica gel (silica 40 g, dichloromethane/ethyl acetate 100:0 to 80:20) to give 574 mg (75%) of the desired product as a yellow solid.

Workup

customwas degassed (vacuum/nitrogen cycles)
customdegassed dioxane (6.87 ml) (nitrogen bubbling with sonication) and a degassed
additionwere added
concentrationconcentrated
custompurified on silica gel (silica 40 g, dichloromethane/ethyl acetate 100:0 to 80:20)

Sources & evidence

ORD record: ord-263631725d1e48a0a3ccd71228cada69
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382218B2

Reaction notes

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