Methyl morpholine oxide → HCID 86654435, 화합물

HRID 1909899노트

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HRID 1909899 반응식
[C:1]([C:5]1[N:6]([C:18]([OH:20])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([Br:14])=[C:9]([Cl:15])[C:8]=2[CH2:16]Br)([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:25]CC1>C(#N)C>[C:1]([C:5]1[N:6]([C:18]([OH:20])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([Br:14])=[C:9]([Cl:15])[C:8]=2[CH:16]=[O:25])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 82029Methyl morpholine oxideHCID 67255556HCID 67255556, 화합물

생성물 1

HCID 86654435HCID 86654435, 화합물수율 47.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a mixture of tert-butyl 5-bromo-7-(bromomethyl)-6-chloro-1H-indole-1-carboxylic acid (7.2 g) and acetonitrile (50 mL) was added 4-methyl morpholine-4-oxide (2.7 g) at room temperature. The reaction mixture was stirred at 50° C. for 7 hours and then at 70° C. overnight. The reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added thereto, and a liquid-separation operation was carried out. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10) to obtain tert-butyl 5-bromo-6-chloro-7-formyl 1H-indole-1-carboxylic acid (2.9 g).

후처리

  1. customat 70° C.
  2. customovernight
  3. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate and water
  4. additionwere added
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10)

출처 및 근거

ORD 기록
ord-e250af7649df42639e7d9b5de7d8657b
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598355B2

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