Isopropyl chloroformate → [4-(1-cyclopropylmethyl-6-ethoxy-3-fluoro-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester

HRID 502275Notes

Reaction equation

HRID 502275 reaction equation
[CH:1]1([CH2:4][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]([F:17])=[C:6]2[C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH2:3][CH2:2]1.[CH:25]([O:28][C:29](Cl)=[O:30])([CH3:27])[CH3:26]>N1C=CC=CC=1>[CH:25]([O:28][C:29](=[O:30])[NH:24][C:21]1[CH:20]=[CH:19][C:18]([C:6]2[N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:13]3[C:8]([C:7]=2[F:17])=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3)=[CH:23][CH:22]=1)([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 594261874-(1-cyclopropylmethyl-6-ethoxy-3-fluoro-1H-indol-2-yl)-phenylamine

Product 1

HCID 59425272[4-(1-cyclopropylmethyl-6-ethoxy-3-fluoro-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(1-cyclopropylmethyl-6-ethoxy-3-fluoro-1H-indol-2-yl)-phenyl amine (30 mg, 0.093 mmol), pyridine (300 μL), and isopropylchloroformate (1 M in toluene, 110 μL, 0.11 mmol) was stirred at room temperature for 90 minutes. The residue was extracted with a mixture of EtOAc and aqueous HCl. The organic layer was washed with H2O and brine and then dried, concentrated and purified by silica gel chromatography (CH2Cl2/Hex, 1:1) to provide [4-(1-cyclopropylmethyl-6-ethoxy-3-fluoro-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (35 mg, 92%) as a white solid.

Workup

  1. extractionThe residue was extracted with a mixture of EtOAc and aqueous HCl
  2. washThe organic layer was washed with H2O and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (CH2Cl2/Hex, 1:1)

Sources & evidence

ORD record
ord-0520cd194e5f45d7b9398fa3511b606a
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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