Tert-Butyl nitrite → 4-(3-Fluoro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 1929170Notes

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

Participants

Conditions

Temperature: 65 °C

Procedure

Tert-butyl nitrite (0.46 ml, 4.45 mmol) is dissolved in 5 ml of dimethylformamide and heated to 65° C. A solution of 143 (1.4 g, 4.45 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 (1.0 g 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 (1.0 g of a brown oil) is further purified by flash-chromatography (hexane/ethyl acetate 7:3)

Sources & evidence

ORD record: ord-d5b0efdf877245feb71ad141229762e4
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183366B2

Reaction notes

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