Ethyl chloroformate → 1-Boc-5-chloro-3-(chloromethyl)-7-azaindole

HRID 509987노트

반응식

HRID 509987 반응식
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([Cl:17])[CH:16]=[C:11]2[C:10]([CH2:18]N(C)C)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22]C(OCC)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([Cl:17])[CH:16]=[C:11]2[C:10]([CH2:18][Cl:22])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 10928Ethyl chloroformateHCID 576192031H-Pyrrolo[2,3-b]pyridine-1-carboxylic acid, 5-chloro-3-[(dimethylamino)methyl]-, 1,1-dimethylethyl ester

생성물 1

HCID 576192411-Boc-5-chloro-3-(chloromethyl)-7-azaindole수율 39.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To 5-chloro-3-dimethylaminomethyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (141, 4.20 g, 13.6 mmol) in 100 mL of toluene, ethyl chloroformate (1.48 mL, 15.5 mmol) was added under nitrogen. The reaction was stirred at room temperature for 2 hours, then concentrated under vacuum and combined with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate was concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 25% ethyl acetate in hexane to provide the desired compound (142, 1.60 g).

후처리

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 25% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-6c6e68c7889b4080a3e4562844effcd1
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

반응 노트

불러오는 중…