Methyl morpholine oxide → HCID 86654435、化合物

HRID 1909899ノート

反応式

HRID 1909899 の反応式
[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]

参加物

4

反応物 2

HCID 82029Methyl morpholine oxideHCID 67255556HCID 67255556、化合物

生成物 1

HCID 86654435HCID 86654435、化合物収率 47.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e250af7649df42639e7d9b5de7d8657b
出典データセット
uspto-grants-2013_12
特許番号
US08598355B2

反応ノート

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