Hydrochloric Acid → HCID 19603701, compound

HRID 1604690Notes

Reaction equation

[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19](=[O:22])[CH2:20]Br)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:23]([C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)#[N:24].C(=O)([O-])[O-].[K+].[K+].Cl>CC(CC)=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19](=[O:22])[CH2:20][N:27]4[C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:25]([C:23]#[N:24])=[CH:26]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-tert-butyl-2-[5-(bromoacetyl)benzofuran-2-yl]thiazole (0.20 g), 3-cyanoindole (75 mg) and potassium carbonate (146 mg) in methylethylketone (3 ml) was stirred at 40° C. for 2 hours. After being cooled to room temperature, the mixture was poured into ice-water and the mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was collected by trituration with diisopropyl ether to give -1-{2-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-2-oxoethyl}indole-3-carbonitrile (0.20 g).

Workup

temperatureAfter being cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was collected by trituration with diisopropyl ether

Sources & evidence

ORD record: ord-9c3fdd354d3049e4aa907d773afcfd7b
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994378

Reaction notes

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