Sodium Carbonate → [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2,6-difluorophenyl)carboxamide

HRID 1524225Notes

Reaction equation

Br[C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[O:8])=[CH:4][CH:3]=1.[Cl:18][C:19]1[C:20](B2OC(C)(C)C(C)(C)O2)=[CH:21][C:22]2[O:26][C:25]([CH3:27])=[N:24][C:23]=2[CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(=O)OCC.[Cl-].[Na+].O>COCCOC.CCO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:18][C:19]1[C:20]([C:2]2[S:6][C:5]([C:7]([NH:9][C:10]3[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=3[F:17])=[O:8])=[CH:4][CH:3]=2)=[CH:21][C:22]2[O:26][C:25]([CH3:27])=[N:24][C:23]=2[CH:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (5-bromo(2-thienyl))-N-(2,6-difluorophenyl)carboxamide (25 mg, 0.08 mmol), 2-(5-chloro-2-methylbenzoxazol-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4) (29 mg, 0.1 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 12 mg) and sodium carbonate (32 mg) in 0.5 ml DME, 0.5 ml EtOH and 0.25 ml water was heated under Ar in microwave reactor at 110° C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to silica gel flash column chromatography to furnish 22.4 mg of [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2,6-difluorophenyl)carboxamide (11) as yellow solid (yield: 55.3%; purity>95%). LC-MS: calcd. for C19H11ClF2N2O2S: 405 (M+1).

Workup

concentrationphase was concentrated

Sources & evidence

ORD record: ord-b363efa132b84d4ba94f06a3ef893146
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079891B2

Reaction notes

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