Triethylamine → Benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylate

HRID 1604676Notes

Reaction equation

HRID 1604676 reaction equation
Cl.[C:2]([C:6]1[N:7]=[C:8]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][C:14]=3[CH:15]=2)[S:9][CH:10]=1)([CH3:5])([CH3:4])[CH3:3].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])=[CH:24]1.C(N(CC)CC)C.CN(C)CC(N)C>ClCCl>[C:2]([C:6]1[N:7]=[C:8]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([C:20]([N:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25]([C:32]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[O:33])=[CH:24]4)=[O:21])=[CH:16][C:14]=3[CH:15]=2)[S:9][CH:10]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 990272-Amino-1-dimethylaminopropaneHCID 8605861HCID 8605861, compoundHCID 196038312-(4-Tert-butylthiazol-2-yl)benzofuran-5-carbonyl chloride hydrochloride

Product 1

HCID 19603790Benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(4-tert-butylthiazol-2-yl)benzofuran-5-carbonyl chloride hydrochloride (140 mg), benzyl indole-3-carboxylate (73.3 mg), triethylamine (0.089 ml) and N,N-dimethylaminopyridine (4 mg) in dichloromethane (4 ml) was stirred under reflux for 7 hours. After being cooled to room temperature, the mixture was treated with N,N-dimethylpropylenediamine (0.018 ml) and diluted with dichloromethane. The dichloromethane solution was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylate (121 mg).

Workup

  1. temperatureunder reflux for 7 hours
  2. washThe dichloromethane solution was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with a mixture of n-hexane and ethyl acetate
  6. additionThe fractions containing the objective compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d86efa4f16234e178628fab15525f0b5
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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