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

HRID 473950ノート

反応式

HRID 473950 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4bd088a2df78400c96fb6b17f6be98a5
出典データセット
uspto-grants-2014_01
特許番号
US08637507B2

反応ノート

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