Cesium carbonate → HCID 59383121, compound

HRID 2355048Notes

Reaction equation

HRID 2355048 reaction equation
ClC1C=CC([C:8]2([C:11]([C:13]3([C:16]4[CH:21]=[CH:20][C:19](Cl)=[CH:18][CH:17]=4)[CH2:15][CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=CC=1.CC1[N:25]=[C:26]([NH:29][C:30](=[O:32])[CH3:31])[S:27]C=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>[CH:8]1([C:11]([C:13]2[CH:15]=[CH:14][C:20]([C:19]3[S:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[N:25][C:18]=3[CH3:17])=[CH:21][CH:16]=2)=[O:12])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 280907N-(4-Methylthiazol-2-yl)acetamideHCID 539671544-Chlorophenyl cyclopropylketone

Product 1

HCID 59383121HCID 59383121, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
150 °C

Procedure

Dry, degassed DMF (90 ml) was added to 4-chlorophenylcyclopropyl ketone (5.0 g, 27.6 mmol), N-(4-Methyl-thiazol-2-yl)-acetamide (3.6 g, 23.1 mmol), Bis(tri-t-butylphosphine) palladium (0) (1.18 g, 2.31 mmol) and caesium carbonate (15.03 g, 46.1 mmol), and the reaction mixture heated to 150° C. for 4 hours. The reaction mixture was filtered through celite and the filtrate reduced in vacuo. The material was purified by column chromatography using as eluant 2:1 to 1:2 Iso-hexane:EtOAc gradient. (M+H) 259.0.

Workup

  1. customDry
  2. customdegassed DMF (90 ml)
  3. filtrationThe reaction mixture was filtered through celite
  4. customThe material was purified by column chromatography

Sources & evidence

ORD record
ord-63d78f5ecddb42788cc09368b5209910
Source dataset
uspto-grants-2010_07
Patent number
US07754746B2

Reaction notes

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