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

HRID 2267869Notes

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]=[C:27]([CH3:29])[CH:26]=[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:28]=[C:27]([CH3:29])[CH:26]=[CH:25][CH:24]=1)[CH:18]=[CH:17][CH:16]=2)=[O:12])[CH3:9]

Participants

Conditions

Temperature: 65 °C

Procedure

Tert-butyl nitrite (0.428 ml, 3.609 mmol) is dissolved in 5 ml of dimethylformamide and heated to 65° C. A solution of 135 (1.1 g, 3.609 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 (930 mg of a brown oil) is further purified by flash-chromatography (hexane/ethyl acetate 7:3).

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 (930 mg of a brown oil) is further purified by flash-chromatography (hexane/ethyl acetate 7:3)

Sources & evidence

ORD record: ord-2720ce829c1d466aa244f8e6913d3b23
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858781B2

Reaction notes

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