Aniline → HCID 11680840, compound

HRID 907094Notes

Reaction equation

HRID 907094 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) was cooled to 0° C. and treated with aniline (0.08 mL, 0.90 mmol). After the addition the reaction was warmed to ambient temperature and after stirring for an additional 16 hours, the reaction mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic phases were washed with saturated NaCl and then dried and concentrated to afford the product. Chromatography (EtOAc/CH2Cl2, 2/98) over silica gel gave 44 mg (51%) of 3-cyano-1-ethyl-1H-indole-6-carboxylic acid phenylamide.

Workup

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

Sources & evidence

ORD record
ord-d6e0cd0684134c35ae52e84228cd8193
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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