Ethyl Acetate → HCID 59335092, compound

HRID 1517948Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:16]([N:19]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:20]2[CH:21]=[CH:22][C:23]3[N:24]([CH2:33][CH3:34])[C:25]4[C:30]([C:31]=3[CH:32]=2)=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:18])=[O:17])[CH:5]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:7]=1.[CH3:43][Si:44]([C:47]#[CH:48])([CH3:46])[CH3:45].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[C:39]([O:38][C:36](=[O:37])[CH2:35][N:19]([S:16]([C:4]1[CH:5]=[C:6]([C:48]#[C:47][Si:44]([CH3:46])([CH3:45])[CH3:43])[CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:17])=[O:18])[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH2:33][CH3:34])[C:25]3[C:30]([C:31]=2[CH:32]=1)=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH3:41])([CH3:40])[CH3:42]

Participants

Conditions

Temperature: 60 °C

Procedure

320 mg tert-butyl [(3-chloro-5-trifluoromethylsulphonyloxy-phenylsulphonyl)-(9-ethyl-9H-carbazol-3-yl)-amino]-acetate are dissolved in 4 ml dimethylformamide. 20 mg copper-1-iodide, 40 mg bis-triphenylphosphine-palladium-dichloride and 210 μl trimethylsilylacetylene are added under argon. Then the mixture is heated to 60° C. for 6 hours and then stirred overnight at ambient temperature. The mixture is then divided between saturated potassium carbonate solution and ethyl acetate. The organic phase is dried on magnesium sulphate and the solvents are eliminated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 100:0 to 95:5).

Workup

customThe organic phase is dried on magnesium sulphate
customThe residue is chromatographed on silica gel (dichloromethane/methanol 100:0 to 95:5)

Sources & evidence

ORD record: ord-745d98ec0b744c3495845ae1a871b0eb
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232312B2

Reaction notes

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