Hexane → 2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-1H-indol-7-amine

HRID 1960414Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:26][CH3:27])[CH:4]1[S:8][C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:13][C:12]=3[N+:23]([O-])=O)=[N:6][CH2:5]1.O.NN.C(OCC)(=O)C.CCCCCC>C(O)C.[C].[Pd]>[CH3:27][O:26][CH:3]([O:2][CH3:1])[CH:4]1[S:8][C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:13][C:12]=3[NH2:23])=[N:6][CH2:5]1

Participants

Conditions

Temperature: 90 °C

Procedure

2-[5-(Dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-7-nitro-1H-indole (100 mg) was suspended in ethanol, and 10% palladium-carbon (50% containing water, 50 mg) was added under nitrogen atmosphere. Hydrazine monohydrate (0.07 mL) was added to the mixture, and the mixture was stirred at 90° C. for 2 hr. Hydrazine monohydrate (0.07 mL) was added again, and the mixture was further stirred at 90° C. for 1 hr. The reaction solution was allowed to cool to room temperature, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=30:70-80:20) to give the title compound (27 mg, yield 29%) as a orange oil.

Workup

stirringthe mixture was further stirred at 90° C. for 1 hr
temperatureto cool to room temperature
filtrationthe catalyst was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained crude product

Sources & evidence

ORD record: ord-d70fe764eb764e65b0828564d7bb22c1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410087B2

Reaction notes

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