Carbon Dioxide → HCID 70561363、化合物

HRID 1477842ノート

反応式

HRID 1477842 の反応式
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[C:11]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:12]=[C:13]([F:16])[CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[Li]CCCC.[C:32](=[O:34])=[O:33]>C1COCC1>[C:20]([O:19][C:18]([NH:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[C:15]2[C:10]=1[CH:9]=[CH:8][N:7]2[CH:6]([C:5]1[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:32]([OH:34])=[O:33])=[O:24])([CH3:22])([CH3:23])[CH3:21]

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 70564826HCID 70564826、化合物HCID 178418339Butyllithium

生成物 1

HCID 70561363HCID 70561363、化合物収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To the mixture of tert-butyl 1-(4-chlorobenzyl)-6-fluoro-1H-indol-4-ylcarbamate (8 g, 0.021 mol) in THF (300 mL) was added dropwise BuLi (2.5 M, 34 mL, 0.084 mol) at −78° C. and the mixture was stirred for another 30 min at −78° C. An excess of dry ice was added and the solution was warmed slowly to room temperature. The resulting mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The aqueous layer was extracted with EA and washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuo to afford the title compound (8 g, yield 89%). LC/MS m/z=363.1 [M-tBu+H]+.

後処理

  1. temperaturethe solution was warmed slowly to room temperature
  2. customThe resulting mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. extractionThe aqueous layer was extracted with EA
  4. washwashed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-74d23dcff78c46648a33adac2d390e24
出典データセット
uspto-grants-2016_08
特許番号
US09403807B2

反応ノート

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