2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → [5-Bromo-4-(4-chlorobenzyl)-7-fluoro-1-oxo-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid methyl ester

HRID 1436216노트

반응식

HRID 1436216 반응식
[Br:1][C:2]1[C:10]2[N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:8]3[CH:19](CC(O)=O)[CH2:20][CH2:21][C:7]=3[C:6]=2[CH:5]=[C:4]([F:26])[CH:3]=1.[N+](=C)=[N-].C(C1C(=O)C(Cl)=C(Cl)C(=[O:35])C=1C#N)#N.C[CH2:45][O:46][C:47]([CH3:49])=[O:48]>C1COCC1.O.[Cl-].[Na+].O>[CH3:45][O:46][C:47](=[O:48])[CH2:49][CH:19]1[C:8]2[N:9]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[C:10]3[C:2]([Br:1])=[CH:3][C:4]([F:26])=[CH:5][C:6]=3[C:7]=2[C:21](=[O:35])[CH2:20]1

참가 물질

7

반응물 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 9550DiazomethaneHCID 18476687[4-(4-Chlorobenzyl)-7-fluoro-5-bromo-1,2,3,4-tetrahydrocyclopenta[B]indol-3-YL]acetic acid

생성물 1

HCID 67021498[5-Bromo-4-(4-chlorobenzyl)-7-fluoro-1-oxo-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid methyl ester

시약·촉매·용매 2

HCID 21881883Oxolane--water (1/1)용매HCID 57417360Sodium chloride; water용매

실험 절차

The methyl ester of the compound of Example 1 step 5 (1.00 g, prepared by treating the corresponding acid with excess diazomethane) in 10 mL of a 9:1 THF/H2O solution was treated with 2.52 g of DDQ. The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture at this time was poured into a separatory funnel containing EtOAc and brine. The combined organic layers were washed with water, brine, dried over anhydrous MgSO4 and concentrated. The resulting material was further purified by flash chromatography eluting with 30% EtOAc/hexane. The chromatography procedure was repeated an additional two times. 350 mg of the above ketone was obtained as a grey solid.

후처리

  1. additionThe reaction mixture at this time was poured into a separatory funnel
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe resulting material was further purified by flash chromatography
  6. washeluting with 30% EtOAc/hexane

출처 및 근거

ORD 기록
ord-ca9b3fdba3864890873b407a1113a4c5
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618994B2

반응 노트

불러오는 중…