Ethyl chloroformate → [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-carbamic acid ethyl ester

HRID 502162Notes

Reaction equation

HRID 502162 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CCOC(C)=O.C([O-])(O)=O.[Na+].O>[CH2:27]([O:26][C:24](=[O:25])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:6][CH:7]=1)[CH3:28]

Participants

6

Reactant 2

HCID 10928Ethyl chloroformateHCID 116017362-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 59425255[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-carbamic acid ethyl esterYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A biphasic mixture of 2-(4-amino-phenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (70 mg, 0.24 mmol), prepared as described in example 1Ga step B, and ethyl chloroformate (0.03 mL, 0.29 mmol) in EtOAc (3 mL) and saturated NaHCO3 (3 mL) is prepared at 0° C. and then allowed to warm to room temperature and stirred for 24 h. The reaction is then diluted with H2O and extracted with EtOAc (2×). The organic phases are washed with H2O and saturated NaCl and then dried and concentrated. Flash chromatography (EtOAc/hexanes 20-40%) gives 48 mg (55%) of [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-carbamic acid ethyl ester as an off-white solid.

Workup

  1. customprepared
  2. customis prepared at 0° C.
  3. extractionextracted with EtOAc (2×)
  4. washThe organic phases are washed with H2O and saturated NaCl
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8b14c3184b1545e69beade56b13bd9b8
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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