Aniline → HCID 11680840, compound

HRID 502112Notes

Reaction equation

HRID 502112 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 the reaction
  2. temperatureis 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-9ed500bd3e054cef89de8ad484892b27
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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