Ethyl bromoacetate → HCID 58824789, compound

HRID 460023Notes

Reaction equation

HRID 460023 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:27])[CH2:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH3:26])=[CH:4][C:3]=1[CH3:28].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:28][C:3]1[CH:4]=[C:5]([C:8](=[O:27])[CH2:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH3:26])[CH:6]=[CH:7][C:2]=1[O:1][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 17972179HCID 17972179, compound2×

Product 1

HCID 58824789HCID 58824789, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 1-(4-hydroxy-3-methylphenyl)-3-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}propan-1-one (intermediate 10, 0.28 g) in dry acetonitrile (15 ml) was treated with ethyl bromoacetate (0.076 ml) and cesium carbonate (0.449 g) and heated at 55° C. for 18 hours. The reaction was filtered, and the filtrate evaporated to give material which was further purified by flash column chromatography using cyclohexane:ethyl acetate (3:1) as eluent to give the title compound as a white solid.

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated
  3. customto give material which
  4. customwas further purified by flash column chromatography

Sources & evidence

ORD record
ord-7223d2dbf4a54ed9a5f8945f48733649
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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