Tert-Butyl nitrite → 4-p-Tolyloxy-1H-indole-2-carboxylic acid ethyl ester

HRID 1929164Notes

Reaction equation

N(OC(C)(C)C)=O.[CH2:8]([O:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[C:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1N)[CH:18]=[CH:17][CH:16]=2)=[O:12])[CH3:9]>CN(C)C=O.C(OCC)C>[CH2:8]([O:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[C:19]([O:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=1)[CH:18]=[CH:17][CH:16]=2)=[O:12])[CH3:9]

Participants

Conditions

Temperature: 65 °C

Procedure

Tert-butyl nitrite (0.176 ml, 1.48 mmol) is dissolved in 5 ml of dimethylformamide and heated to 65° C. A solution of 139 (460 mg, 1.48 mmol) in 5 ml of dimethylformamide is added dropwise and the mixture is stirred of additional 10 minutes. The brown solution is cooled to room temperature, diluted with diethyl ether and washed with 2N HCl and brine. The organic layers are dried over sodium sulphate and evaporated. The crude product (420 mg of a brown oil) is further purified by flash-chromatography (hexane/ethyl acetate 9:1).

Workup

temperatureThe brown solution is cooled to room temperature
washwashed with 2N HCl and brine
dry with materialThe organic layers are dried over sodium sulphate
customevaporated
customThe crude product (420 mg of a brown oil) is further purified by flash-chromatography (hexane/ethyl acetate 9:1)

Sources & evidence

ORD record: ord-987b99243775410bb086c92d0da7f7da
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183366B2

Reaction notes

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