Tert-Butyl nitrite → HCID 66841670, compound

HRID 1929181Notes

Reaction equation

HRID 1929181 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])[C:26]([F:30])=[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]([F:30])=[C:27]([F:29])[CH:28]=1)[CH:18]=[CH:17][CH:16]=2)=[O:12])[CH3:9]

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 668420244-(2-Amino-4,5-difluoro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 66841670HCID 66841670, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

Tert-butyl nitrite (0.575 ml, 4.85 mmol) is dissolved in 5 ml of dimethylformamide and heated to 65° C. A solution of 151 (1.6 g, 4.85 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 (1.78 g of a brown oil) is further purified by flash-chromatography (hexane/ethyl acetate 9:1).

Workup

  1. temperatureThe brown solution is cooled to room temperature
  2. washwashed with 2N HCl and brine
  3. dry with materialThe organic layers are dried over sodium sulphate
  4. customevaporated
  5. customThe crude product (1.78 g of a brown oil) is further purified by flash-chromatography (hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-bdc7de44b31647c5b424988a7266f3f2
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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