1-Cyclopropylethanol → HCID 59424955, compound

HRID 502255Notes

Reaction equation

HRID 502255 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:24]3[CH2:26][CH2:25]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:11]=3)=[CH:4][CH:3]=1.C1C([N+]([O-])=O)=CC=C([Cl-][C:37]([O-])=[O:38])C=1.[CH:40]1([CH:43]([OH:45])[CH3:44])[CH2:42][CH2:41]1>N1C=CC=CC=1.O.C(Cl)Cl>[CH:40]1([CH:43]([O:45][C:37](=[O:38])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]([CH:24]4[CH2:26][CH2:25]4)[C:10]4[C:15]([C:16]=3[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:11]=4)=[CH:4][CH:3]=2)[CH3:44])[CH2:42][CH2:41]1

Participants

6

Reactant 2

HCID 791041-CyclopropylethanolHCID 59426202HCID 59426202, compound

Product 1

HCID 59424955HCID 59424955, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 2-(4-aminophenyl)-1-cyclopropyl-6-(2-methoxyethoxy)indole-3-carbonitrile (35 mg, 0.1 mmol), 4-nitrophenylchloroformate (50 mg, 0.25 mmol) in pyridine (2.0 mL) is stirred at 35° C. for 2 h, followed by the addition of 1-cyclopropylethanol (98 μL, 1.0 mmol). The mixture is then stirred at 60° C. overnight and diluted with water (10 mL) and DCM (5 mL). The organic is washed with water (3×5 mL), HCl (2N, 3×5 mL), saturated NaHCO3 (3×5 mL) and chromatographed (silica gel, EtOAc/DCM, 0.5/9.5) to provide the title compound, {4-[3-cyano-1-cyclopropyl-6-(2-methoxyethoxy)indol-2-yl]phenyl}carbamic acid 1-cyclopropylethyl ester (22 mg, 48%).

Workup

  1. stirringThe mixture is then stirred at 60° C. overnight
  2. washThe organic is washed with water (3×5 mL), HCl (2N, 3×5 mL), saturated NaHCO3 (3×5 mL)
  3. customchromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

Sources & evidence

ORD record
ord-0e1c32eb09ec44829e802bb3fd34635f
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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