(Dimethyl sulfide)trihydroboron → 7-bromo-2-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

HRID 473950노트

반응식

HRID 473950 반응식
CSC.B.[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:14][C:13](=O)[CH:12]([CH3:16])[O:11][C:10]=2[CH:17]=1>C1COCC1>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:14][CH2:13][CH:12]([CH3:16])[O:11][C:10]=2[CH:17]=1

참가 물질

4

반응물 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 226231297-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

생성물 1

HCID 580646527-bromo-2-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Borane dimethyl sulfide complex (2 M solution in THF, 0.414 mL, 0.828 mmol) was added at room temperature to a solution of 7-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one A-2 (100.0 mg, 0.414 mmol) in anhydrous THF (4.10 mL) under an atmosphere of argon. The reaction mixture was heated to reflux for 2 h, cooled to room temperature, quenched with methanol (1.0 mL), stirred for 30 mins and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient) to give 7-bromo-2-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine A-3 (92.9 mg, Yield=98%). MS (ESI) [M+1]+ 228, 230.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. customquenched with methanol (1.0 mL)
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-4bd088a2df78400c96fb6b17f6be98a5
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637507B2

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