Isopropyl chloroformate → HCID 118079263, compound

HRID 1485693Notes

Reaction equation

HRID 1485693 reaction equation
C(N(CC)C(C)C)(C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21](=[O:23])[CH3:22])[C@@H:16]([CH3:24])[CH2:15][NH:14]2.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>ClCCCl>[C:21]([N:17]1[C:18]2[C:13](=[CH:12][C:11]([Br:10])=[CH:20][CH:19]=2)[N:14]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:15][C@@H:16]1[CH3:24])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 118078861(S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

Product 1

HCID 118079263HCID 118079263, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

N,N-Diisopropylethylamine (0.973 mL, 5.57 mmol) was added to a solution of (S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.500 g, 1.858 mmol) and isopropyl chloroformate (1.0 M in toluene, 2.79 mL, 2.79 mmol) in 1,2-dichloroethane (10.0 mL), and the mixture stirred at 50° C. for 16 h. The reaction mixture was concentrated to afford a yellow oil. This material was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford (S)-isopropyl 4-acetyl-7-bromo-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.558 g, 85%) as an off-white solid. MS (ESI, pos. ion) m/z 355, 357 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford a yellow oil
  3. customThis material was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 0-50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-8fade10191514e06a86459ab733bfda6
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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