Sodium Azide → Propyl (7-azido-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

HRID 1944022노트

반응식

HRID 1944022 반응식
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH2:11][CH:12](OS(C)(=O)=O)[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:20][C:21]([O:23][CH2:24][CH2:25][CH3:26])=[O:22].[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C>[N:27]([CH:12]1[CH2:11][N:9]2[C:10]3[C:6]([C:7]([CH2:20][C:21]([O:23][CH2:24][CH2:25][CH3:26])=[O:22])=[C:8]2[CH2:14][CH2:13]1)=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])=[N+:28]=[N-:29]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86645393Propyl {4-fluoro-7-[(methylsulfonyl)oxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}acetate

생성물 1

HCID 86645392Propyl (7-azido-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a stirred solution of propyl {4-fluoro-7-[(methylsulfonyl)oxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}acetate (1 eq) in DMF (0.15M) at 0° C. was added sodium azide (1.2 eq). The reaction mixture was stirred at 60° C. for 6 h. The reaction was quenched by addition of water and NH4Cl, extracted with EtOAc, washed with water, brine, dried and evaporated. The residue was purified by column chromatography on silica gel eluting with EtOAc/Hexanes (0 to 50%) to give the desired material as a yellow oil.

후처리

  1. customThe reaction was quenched by addition of water and NH4Cl
  2. extractionextracted with EtOAc
  3. washwashed with water, brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with EtOAc/Hexanes (0 to 50%)

출처 및 근거

ORD 기록
ord-d3e80184fdcd4a93a52ef8e7e3e447ac
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394819B2

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