Carbon Dioxide → HCID 70561363, 화합물

HRID 1477842노트

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HRID 1477842 반응식
[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]

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 70564826HCID 70564826, 화합물HCID 178418339Butyllithium

생성물 1

HCID 70561363HCID 70561363, 화합물수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-74d23dcff78c46648a33adac2d390e24
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403807B2

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