2-Furancarbonyl chloride → HCID 123316250, compound

HRID 1485697Notes

Reaction equation

HRID 1485697 reaction equation
[CH3:1][C@H:2]1[CH2:11][NH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:12]3[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]3)[CH:8]=2)[N:3]1[C:21](=[O:23])[CH3:22].C(N(CC)C(C)C)(C)C.[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38](Cl)=[O:39]>O1CCOCC1>[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38]([N:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:12]3[O:16][C:15]([CH3:17])([CH3:18])[C:14]([CH3:20])([CH3:19])[O:13]3)[CH:8]=2)[N:3]([C:21](=[O:23])[CH3:22])[C@@H:2]([CH3:1])[CH2:11]1)=[O:39]

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 131736753HCID 131736753, compound

Product 1

HCID 123316250HCID 123316250, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A 100 mL round bottom flask fitted with a nitrogen inlet, and stir bar was charged with (S)-1-(2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinoxalin-1(2H)-yl)ethanone (0.8 g, 2.53 mmol), 1,4-dioxane (30 ml), N,N-diisopropylethylamine (2.65 mL, 15.18 mmol) and furan-2-carbonyl chloride (0.991 g, 7.59 mmol). The reaction mixture was purged with nitrogen and heated to 50° C. for 2 h. The mixture was cooled to rt and diluted with ethyl acetate (100 mL). The mixture was then washed with brine (50 mL), and the organic layer was concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 9:1 hexanes-ethyl acetate) to afford (S)-1-(4-(furan-2-carbonyl)-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinoxalin-1(2H)-yl)ethanone (0.69 g, 66% yield) as a colorless foam. MS (ESI, pos. ion) m/z 411 [M+1]+.

Workup

  1. customA 100 mL round bottom flask fitted with a nitrogen inlet
  2. customThe reaction mixture was purged with nitrogen
  3. temperatureThe mixture was cooled to rt
  4. additiondiluted with ethyl acetate (100 mL)
  5. washThe mixture was then washed with brine (50 mL)
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (eluting with 9:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-af2851e8a6ef4c9d9e5c5a4b61d4f065
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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