Isopropyl chloroformate → HCID 46946240, compound

HRID 502288Notes

Reaction equation

HRID 502288 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:11]=3)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:36]([O:39][C:40](Cl)=[O:41])([CH3:38])[CH3:37]>C(OCC)(=O)C>[CH:36]([O:39][C:40](=[O:41])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:26]3[CH2:27][CH2:28][CH2:29]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:11]=3)=[CH:4][CH:3]=1)([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 11430Potassium CarbonateHCID 59425475HCID 59425475, compound

Product 1

HCID 46946240HCID 46946240, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(4-amino-phenyl)-1-cyclobutyl-6-(tetrahydro-pyran-4-yloxy)-1H-indole-3-carbonitrile (897.8 mg, 2.32 mmol), K2CO3 (7 mL), and ethyl acetate (7 mL) was added iPrOCOCl (6.9 mL, 1 M in toluene, 6.96 mmol). The resulting mixture was stirred at room temperature overnight. The organic layer was washed with brine, dried over Mg2SO4, concentrated and purified on silica gel (EtOAc/hexanes, 10% to 30%) to provide the product (1.01 g, 92%) as white solid.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Mg2SO4
  3. concentrationconcentrated
  4. custompurified on silica gel (EtOAc/hexanes, 10% to 30%)

Sources & evidence

ORD record
ord-8cabe85707314947b8cbe835a4ac5c89
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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