Cesium carbonate → HCID 59323903, compound

HRID 1715183Notes

Reaction equation

HRID 1715183 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]1[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:17]2[S:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[N:14][C:13]=2[CH3:12])=[CH:3][C:4]=1[F:11])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 280907N-(4-Methylthiazol-2-yl)acetamideHCID 219385811-(4-Bromo-2-fluorophenyl)ethan-1-one

Product 1

HCID 59323903HCID 59323903, compound

Reagents, catalysts & solvents 1

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)Catalyst

Conditions

Temperature
150 °C

Procedure

Dry, degassed DMF (25 ml) is added to 1-(4-bromo-2-fluoro-phenyl)-ethanone (WO 2003095441) (1.25 g, 5.76 mmol), N-(4-methyl-thiazol-2-yl)-acetamide (0.75 g, 4.80 mmol), Bis (tri-t-butylphosphine) palladium (0) (0.245 g, 0.48 mmol) and caesium carbonate (3.13 g, 9.60 mmol), and the reaction mixture heated to 150° C. for 4 hours. The reaction mixture is filtered through celite and the filtrate reduced in vacuo. Purification of the crude product by chromatography on silica eluting with 2:1 iso-hexane:EtOAc affords the title compound as a yellow solid. (MH+) 293.25

Workup

  1. customDry
  2. customdegassed DMF (25 ml)
  3. filtrationThe reaction mixture is filtered through celite
  4. customPurification of the crude product by chromatography on silica eluting with 2:1 iso-hexane

Sources & evidence

ORD record
ord-ec4794717c754c57bb3bdc52ed1f21b3
Source dataset
uspto-grants-2010_09
Patent number
US07799810B2

Reaction notes

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