Cyclopentyl chloroformate → cyclopentyl N-[4-(3-cyano-1-cyclobutyl-6-ethoxy-indol-2-yl)phenyl]-N-ethyl-carbamate

HRID 1009649Notes

Reaction equation

HRID 1009649 reaction equation
[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3)[C:7]([C:17]#[N:18])=[C:6]2[C:19]2[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH2:4][CH2:3][CH2:2]1.Cl[C:29]([O:31][CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:30].ClC([O-])=O>N1C=CC=CC=1>[CH:32]1([O:31][C:29](=[O:30])[N:25]([C:22]2[CH:21]=[CH:20][C:19]([C:6]3[N:5]([CH:1]4[CH2:2][CH2:3][CH2:4]4)[C:13]4[C:8]([C:7]=3[C:17]#[N:18])=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=4)=[CH:24][CH:23]=2)[CH2:26][CH3:27])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 2735892Cyclopentyl chloroformateHCID 21226386CarbonochloridateHCID 497723701-Cyclobutyl-6-ethoxy-2-[4-(ethylamino)phenyl]indole-3-carbonitrile

Product 1

HCID 49772432cyclopentyl N-[4-(3-cyano-1-cyclobutyl-6-ethoxy-indol-2-yl)phenyl]-N-ethyl-carbamateYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Cyclobutyl-6-ethoxy-2-(4-ethylaminophenyl)-1H-indole-3-carbonitrile (35 mg, 0.10 mmol), prepared as in example 1CO, step C, is dissolved in pyridine (300 μL). Cyclopentyl chloroformate (25 μL, 0.17 mmol) is added. The reaction mixture is stirred at room temperature for 2.5 h. More chloroformate (10 μL, 0.07 mmol) is added to drive the reaction to completion. After an additional 90 min of stirring, the reaction mixture is partitioned between aqueous HCl and EtOAc. The organic layer is dried and concentrated. Purification by silica gel chromatography yields [4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-ethyl-carbamic acid cyclopentyl ester (41 mg, 87%) as a white solid.

Workup

  1. customthe reaction to completion
  2. stirringAfter an additional 90 min of stirring
  3. customthe reaction mixture is partitioned between aqueous HCl and EtOAc
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-cc9734e799ab4cd0bb0034aae8a6ddd4
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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