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

HRID 1524226Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([NH:9][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[O:11])[C:7]=1[F:8].[CH3:18][C:19]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][C:22]2[N:23]=[CH:24][S:25][C:21]=2[CH:20]=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>[F:17][C:5]1[CH:4]=[CH:3][CH:2]=[C:7]([F:8])[C:6]=1[NH:9][C:10]([C:12]1[S:13][C:14]([C:27]2[C:19]([CH3:18])=[CH:20][C:21]3[S:25][CH:24]=[N:23][C:22]=3[CH:26]=2)=[CH:15][CH:16]=1)=[O:11]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (5-bromo(2-thienyl)-N-(2,6-difluorophenyl)carboxamide (22 mg, 0.07 mmol), 6-methyl-5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))benzothiazole (14) (19 mg, 0.07 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 8 mg) and sodium carbonate (22 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 prep HPLC chromatography to furnish 22.8 mg of N-(2,6-difluorophenyl)[5-(6-methylbenzothiazol-5-yl)(2-thienyl)]carboxamide (15) as white solid (yield: 84.3%; purity>95%). LC-MS: calcd. for C19H12F2N2OS2: 387 (M+1).

Workup

concentrationphase was concentrated

Sources & evidence

ORD record: ord-e5a1e7ff6c00401b92e4ffddd5ade254
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079891B2

Reaction notes

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