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

HRID 1604675
Notes
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Reaction equation

HRID 1604675 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 312ChlorideHCID 14798Sodium HydroxideHCID 196037484-Tert-butyl-2-[5-(3-chloropropyl)benzofuran-2-yl]thiazoleHCID 196038046-Methyl-1H-indole-3-carbonitrile

Product 1

HCID 196036914-Tert-butyl-2-{5-[3-(3-cyano-6-methylindole-1-yl)propyl]-benzofuran-2-yl}thiazoleYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureAfter the mixture was cooled to room temperature
  2. filtrationthe insolble mass was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a syrup
  5. washeluted with a mixture of n-hexane and ethyl acetate
  6. additionThe fraction containing the objective compound
  7. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes