2-Furancarbonyl chloride → HCID 118080017, compound

HRID 1485700Notes

Reaction equation

HRID 1485700 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[C@@H:7]([CH3:18])[CH2:6][NH:5]2.C(N(CC)C(C)C)(C)C.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](Cl)=[O:34]>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:17])[C:13]([F:14])([F:16])[F:15])[C@@H:7]([CH3:18])[CH2:6][N:5]2[C:33]([C:29]1[O:28][CH:32]=[CH:31][CH:30]=1)=[O:34]

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 118079994HCID 118079994, compound

Product 1

HCID 118080017HCID 118080017, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 100 mL round bottomed flask fitted with a nitrogen inlet was charged with (S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)-2,2,2-trifluoroethanone (1.54 g, 4.77 mmol), 1,2-dichloroethane (45 mL), and N,N-diisopropylethyl amine (2.497 mL, 14.30 mmol). The mixture stirred for 5 min and then furan-2-carbonyl chloride (0.940 mL, 9.53 mmol) was slowly added. The reaction stirred at room temperature for 2 h and was then concentrated. The residue was purified via column chromatography (eluting with 3:2 hexanes/ethyl acetate) to afford (S)-1-(6-bromo-4-(furan-2-carbonyl)-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)-2,2,2-trifluoroethanone (1.07 g, 54%) as an off-white solid. MS (ESI, pos. ion) m/z 417, 419 [M+1]+.

Workup

  1. customA 100 mL round bottomed flask fitted with a nitrogen inlet
  2. stirringThe reaction stirred at room temperature for 2 h
  3. concentrationwas then concentrated
  4. customThe residue was purified via column chromatography (eluting with 3:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-c58a0f277ed84778b48b2c43b1a104d1
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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