Chloride → 4-Tert-butyl-2-{5-[3-(3-cyano-6-methylindole-1-yl)propyl]-benzofuran-2-yl}thiazole

HRID 1604675Notes

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]([CH2:19][CH2:20][CH2:21]Cl)=[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][C:30]([CH3:34])=[CH:31][CH:32]=2)[NH:27][CH:26]=1)#[N:24].[OH-].[Na+].[Cl-]>O1CCCC1>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][N:27]4[C:28]5[C:33](=[CH:32][CH:31]=[C:30]([CH3:34])[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: 60 °C

Procedure

A mixture of 4-tert-butyl-2-[5-(3-chloropropyl)-benzofuran-2-yl]thiazole (0.19 g), 3-cyano-6-methylindole (73 mg), sodium hydroxide (90 mg) and small amount of cetyl trymethylammonium chloride in tetrahydrofuran (1 ml) was stirred at 60° C. for 1 day. After the mixture was cooled to room temperature, the insolble mass was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fraction containing the objective compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-[3-(3-cyano-6-methylindole-1-yl)propyl]-benzofuran-2-yl}thiazole (90 mg).

Workup

temperatureAfter the mixture was cooled to room temperature
filtrationthe insolble mass was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customto give a syrup
washeluted with a mixture of n-hexane and ethyl acetate
additionThe fraction containing the objective compound
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-38a69cfe465347158e7ba1061b450531
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994378

Reaction notes

Loading…