Sodium Carbonate → HCID 68062149, compound

HRID 1524234Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([NH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[O:10])[CH:7]=1.O1[CH2:21][CH2:20]OB1.[C:22](=[O:25])([O-])[O-].[Na+].[Na+].CC(=O)O[CH2:31][CH3:32].[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>[CH3:7][C:6]1[C:5]2[CH:4]=[C:20]([CH3:21])[C:31]([C:13]3[S:12][C:11]([C:9]([NH:8][C:6]4[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=4[F:16])=[O:10])=[CH:15][CH:14]=3)=[CH:32][C:22]=2[O:25][N:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (5-bromo(2-thienyl)-N-(2-fluorophenyl)carboxamide (22 mg, 0.073 mmol), 2-(3,5-dimethylbenzo[d]isoxazol-6-yl)-4,4,5,5-tetramethyl(1,3,2-dioxaborolane (28) (20 mg, 0.073 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 8 mg) and sodium carbonate (29 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 (0-80% B; A: hexane; B: 50% EA in hexane) to furnish 22.4 mg of [5-(3,5-dimethylbenzo[d]isoxazol-6-yl)(2-thienyl)]-N-(2-fluorophenyl)carboxamide (30) as light yellow solid (yield: 83.7%; purity>95%). LC-MS: calcd. for C20H15FN2O2S: 367 (M+1).

Workup

concentrationphase was concentrated

Sources & evidence

ORD record: ord-c0c13b1652c4478cb0fdf9538c406323
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079891B2

Reaction notes

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