Sodium Carbonate → [5-(5-chlorobenzothiazol-6-yl)(2-thienyl)]-N-(2-fluorophenyl)carboxamide

HRID 1524231Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (5-bromo(2-thienyl))-N-(2-fluorophenyl)carboxamide (9, 18 mg, 0.06 mmol), 5-chloro-6-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))benzothiazole (20) (17 mg, 0.06 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 7 mg) and sodium carbonate (19 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 chromatography (0-60% B; A: hexane; B: 50% EA in hexane) to furnish 16.7 mg of [5-(5-chlorobenzothiazol-6-yl)(2-thienyl)]-N-(2-fluorophenyl)carboxamide (23) as white solid (yield: 71.6%; purity>95%). LC-MS: calcd. for C18H10FClN2OS2: 389 (M+1).

Workup

concentrationphase was concentrated

Sources & evidence

ORD record: ord-d43fbc27bebc482fa150b62578f61e15
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079891B2

Reaction notes

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