Aniline → HCID 11680840, compound

HRID 1009523Notes

Reaction equation

HRID 1009523 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12](Cl)=[O:13])=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[CH:4]=1)#[N:2].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCOC(C)=O.C(Cl)Cl>C1COCC1.O>[C:18]1([NH:17][C:12]([C:8]2[CH:7]=[C:6]3[C:11]([C:3]([C:1]#[N:2])=[CH:4][N:5]3[CH2:15][CH3:16])=[CH:10][CH:9]=2)=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 21226138Dichloromethane ethylacetateHCID 59424944HCID 59424944, compound

Product 1

HCID 11680840HCID 11680840, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-cyano-1-ethyl-1H-indole-6-carbonyl chloride (70 mg, 0.30 mmol) in THF (5 mL) is cooled to 0° C. and treated with aniline (0.08 mL, 0.90 mmol). After the addition, the reaction is warmed to ambient temperature and after stirring for an additional 16 hours, the reaction mixture is diluted with H2O and extracted with EtOAc (2×). The combined organic phases are washed with saturated NaCl and then dried and concentrated to afford the product. Chromatography (EtOAc/CH2Cl2, 2/98) over silica gel gives 44 mg (51%) of 3-cyano-1-ethyl-1H-indole-6-carboxylic acid phenylamide.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction is warmed to ambient temperature
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic phases are washed with saturated NaCl
  5. customdried
  6. concentrationconcentrated
  7. customto afford the product

Sources & evidence

ORD record
ord-cbe69d1aaa614dbd9ddaefdb689a2bbf
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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