Benzyl chloroformate → HCID 58562610, compound

HRID 2175522Notes

Reaction equation

HRID 2175522 reaction equation
C(=O)(O)[O-].[Na+].[F:6][C:7]([F:20])([F:19])[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[C:11]2[NH2:18].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C(OCC)(=O)C>[F:20][C:7]([F:6])([F:19])[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[C:11]2[NH:18][C:22](=[O:23])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 27359586-(trifluoromethyl)quinolin-4-amine

Product 1

HCID 58562610HCID 58562610, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A rapidly stirred mixture of ethyl acetate and saturated aqueous sodium bicarbonate containing commercially available 6-(trifluoromethyl)quinolin-4-amine (558 mg, 2.63 mmol) was cooled to 0° C. and treated dropwise with benzyl chloroformate (1.10 mL, 3.29 mmol). After stirring overnight warming to room temperature, the aqueous layer was removed and the organic layer concentrated in vacuo. Purification of the residue by flash chromatography (silica gel, 0-20% MeOH/Ethyl acetate) yielded the product.

Workup

  1. temperaturewarming to room temperature
  2. customthe aqueous layer was removed
  3. concentrationthe organic layer concentrated in vacuo
  4. customPurification of the residue by flash chromatography (silica gel, 0-20% MeOH/Ethyl acetate)
  5. customyielded the product

Sources & evidence

ORD record
ord-6d5a335a0cc7419893f6f04d9d521260
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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