Dimethylformamide → 9-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carbaldehyde

HRID 1498087ノート

反応式

HRID 1498087 の反応式
C([Mg]Br)C.[Br:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]3[N:11]([CH:15]=[C:16](I)[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1.CN(C)[CH:23]=[O:24]>C(OCC)C.O1CCCC1>[Br:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]3[N:11]([CH:15]=[C:16]([CH:23]=[O:24])[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 582048589-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepineHCID 178418443HCID 178418443、化合物

生成物 1

HCID 582043679-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
15 °C

実験手順

Ethylmagnesium bromide in ethyl ether (3.0 M, 3.472 mL) was added dropwise to a solution of 9-bromo-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (1173 mg, 3.000 mmol) in 20 ml of tetrahydrofuran at −30° C. The mixture was stirred at this temperature for 20 min and allowed to warm to 15° C. The mixture was cooled to −25° C. again and N,N-dimethylformamide (929.2 uL, 12.00 mmol) was added. The mixture was left for 18 hours. The mixture was quenched with sat. aq. NH4Cl and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried over mgSO4 and concentrated in vacuum. Yield 0.92 g. MS: 293.1

後処理

  1. temperatureThe mixture was cooled to −25° C. again
  2. waitThe mixture was left for 18 hours
  3. customThe mixture was quenched with sat. aq. NH4Cl
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with water, brine
  6. customdried over mgSO4
  7. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-7bfe147313f5442ba1f435f72e2b3378
出典データセット
uspto-grants-2015_12
特許番号
US09198918B2

反応ノート

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