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

HRID 2267869
Notes
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Reaction equation

HRID 2267869 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 668415234-(2-Amino-5-methyl-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668417024-m-Tolyloxy-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

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

  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 (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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes