1,2-Dichloroethane → HCID 118080266, compound

HRID 1485751Notes

Reaction equation

HRID 1485751 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C@@H:7]([CH3:21])[CH2:8][N:9]2[C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][N:13]=2)=[CH:4][CH:3]=1.ClCCCl.C(N(CC)C(C)C)(C)C.[C:35](Cl)(=[O:37])[CH3:36]>C(OCC)(=O)C>[O:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:12]([N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=3)[N:6]([C:35](=[O:37])[CH3:36])[C@@H:7]([CH3:21])[CH2:8]2)=[N:13]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 118079803HCID 118079803, compound

Product 1

HCID 118080266HCID 118080266, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A reaction vial was charged with (S)-3-(7-bromo-3-methyl-3,4-dihydroquinoxalin-1(2H)-yl)benzo[d]isoxazole (10.33 mg, 0.03 mmol) and 1,2-dichloroethane (0.30 mL). N,N-Diisopropylethylamine (0.026 mL, 0.150 mmol) and acetyl chloride (6.4 μl, 0.090 mmol) were added, and the mixture stirred at 50° C. for 1.5 h. The reaction was diluted with ethyl acetate and washed with brine. The aqueous layer was separated and washed with ethyl acetate, and the combined organic layers were concentrated under a stream of nitrogen to afford (S)-1-(4-(benzo[d]isoxazol-3-yl)-6-bromo-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.012 g, 0.03 mmol) which was used without purification. MS (ESI, pos. ion) m/z 386

Workup

  1. customA reaction
  2. washwashed with brine
  3. customThe aqueous layer was separated
  4. washwashed with ethyl acetate
  5. concentrationthe combined organic layers were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-cfd96c7eef22495a87590e7a3fa84d14
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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