Sodium Carbonate → 4-(3-Fluoro-phenyl)-6-methyl-pyridine-2-carboxylic acid (4-methyl-thiazol-2-yl)-amide

HRID 552485Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]([C:10]2[CH:15]=[C:14](Br)[CH:13]=[C:12]([CH3:17])[N:11]=2)=[O:9])[S:5][CH:6]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]([C:10]2[CH:15]=[C:14]([C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([F:18])[CH:24]=3)[CH:13]=[C:12]([CH3:17])[N:11]=2)=[O:9])[S:5][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 150 mg (0.48 mmol) of 4-Bromo-6-methyl-pyridine-2-carboxylic acid (4-methyl-thiazol-2-yl)-amide, 71 mg (0.5 mmol, 1.05 equiv.) of 3-Fluorophenyl-boronic acid in 2 ml of dioxane were added 0.5 ml of 2M sodium carbonate solution and the mixture was purged with Argon for 10 min. Then 25 mg (0.096 mmol, 0.2 equiv.) of Triphenylphosphine and 10.8 mg (0.048 mmol, 0.1 equiv.) of Palladium acetate were added and the mixture was stirred under Argon atmosphere for 24 h at 90° C. The reaction was allowed to cool to r.t., taken up in two times in ethyl acetate and evaporated to dryness. The residue was separated by flash chromatography on silicagel (heptane/ethyl acetate 4:1) to yield the title compound (111 mg, 71%) as a yellow solid, MS (ISP): m/e=328.0 (M+H)+.

Workup

customthe mixture was purged with Argon for 10 min
temperatureto cool to r.t.
customevaporated to dryness
customThe residue was separated by flash chromatography on silicagel (heptane/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-7b4b6f8c219549e3baa96fd0b71e4735
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951824B2

Reaction notes

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