Dimethylformamide → 4-(4-Isopropyl-phenyl)-1-(3-methane-sulphonyl-benzyl)-5-propargyloxy-phenyl-methanone

HRID 1046354Notes

Reaction equation

HRID 1046354 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=C[C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=O.[C:23]([O-:26])([O-])=O.[K+].[K+].Cl[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([S:36]([CH3:39])(=[O:38])=[O:37])[C:31]=1C.[CH3:41]N(C)C=O>>[CH:20]([C:17]1[CH:16]=[CH:15][C:14]([C:12]2[C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:7]([CH:23]=[O:26])([CH2:41][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([S:36]([CH3:39])(=[O:37])=[O:38])[CH:31]=3)[CH2:2][CH:3]=2)=[CH:19][CH:18]=1)([CH3:21])[CH3:22]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 213497981-Chloro-methyl-3-methanesulphonyl-benzeneHCID 45139628(2-Amino-5-(prop-2-yn-1-yloxy)phenyl)(4-isopropylphenyl)methanone

Product 1

HCID 866043814-(4-Isopropyl-phenyl)-1-(3-methane-sulphonyl-benzyl)-5-propargyloxy-phenyl-methanone

Conditions

Temperature
100 °C

Procedure

A mixture of 100 mg (0.34 mmol) (2-amino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone, 80 mg (0.58 mmol) K2CO3 and 77 mg (0.375 mmol) 1-chloro-methyl-3-methanesulphonyl-benzene in 1 ml dimethylformamide is stirred at 80° C. for 6 h and at 100° C. for 3 h. Then the reaction mixture is poured onto water and extracted with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1) to afford the title compound as a yellow foam.

Workup

  1. additionThen the reaction mixture is poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1)

Sources & evidence

ORD record
ord-e909d337b1ed4f4c8ef710dbef35d7b8
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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