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

HRID 907143Notes

Reaction equation

HRID 907143 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) was prepared at 0° C. and then allowed to warm to room temperature and stirred for 24 h. The reaction was then diluted with H2O and extracted with EtOAc (2×). The organic phases were washed with H2O and saturated NaCl and then dried and concentrated. Flash chromatography (EtOAc/hexanes 20-40%) gave 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. customwas prepared at 0° C.
  3. extractionextracted with EtOAc (2×)
  4. washThe organic phases were washed with H2O and saturated NaCl
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-73c8b53af8384f8899ed62fa054445c5
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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