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

HRID 1629057노트

반응식

HRID 1629057 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
15 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-33137228023b46e695f0443e0fe64e02
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785626B2

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