Chlorosuccinimide → 1-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole

HRID 1634715노트

반응식

HRID 1634715 반응식
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl:19]N1C(=O)CCC1=O>CN(C=O)C>[Cl:19][C:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[C:6]([O:5][CH2:4][C@@H:2]2[CH2:3][O:1]2)=[CH:7][CH:8]=1.[Cl:19][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:6]=1[O:5][CH2:4][C@@H:2]1[CH2:3][O:1]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

참가 물질

5

반응물 2

HCID 31398ChlorosuccinimideHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

생성물 2

HCID 590329461-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazoleHCID 590329593-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-[(2S)-oxiranylmethoxy]-9H-carbazole (0.50 g, 2.09 mmol) and N-chlorosuccinimide (0.280 g, 2.09 mmol) in 5 mL dry DMF was stirred at ambient temperature for 48 hours. The reaction mixture was partitioned with EtOAc and H2O. The organic phase was washed with H2O and dried with Na2SO4. The solvent was removed (rotovap) and the residue purified by flash chromatography (methylene chloride-hexane-1:1) afforded 0.10 g of the title compound plus 0.50 g of 3-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole.

후처리

  1. customThe reaction mixture was partitioned with EtOAc and H2O
  2. washThe organic phase was washed with H2O
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed (rotovap)
  5. customthe residue purified by flash chromatography (methylene chloride-hexane-1:1)

출처 및 근거

ORD 기록
ord-420bbba7dd7e4683b5048af95a46fd4b
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506901B2

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