Carbon Dioxide → 5-methoxy-1H-indole-7-carboxylic acid

HRID 661339노트

반응식

HRID 661339 반응식
Br[C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[Li]CCCC.[C:18](=[O:20])=[O:19]>C1COCC1.CCCCCC>[CH3:12][O:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([C:18]([OH:20])=[O:19])[CH:3]=1)[NH:9][CH:8]=[CH:7]2

참가 물질

6

반응물 3

HCID 280Carbon DioxideHCID 198041607-Bromo-5-methoxy-1H-indoleHCID 178418339Butyllithium

생성물 1

HCID 597466045-methoxy-1H-indole-7-carboxylic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A solution of 7-Bromo-5-methoxy-1H-indole (described in WO 2002028861) in THF was treated with 2 eq. of a solution of n-BuLi in n-hexane (1.6M) at 5° and after 30 min at this temperature was cooled to −75°. Dry ice (excess) was added and after 15 mins the mixture was quenched with H2O and washed with EtOAc. After acidification of the aqueous layer and extraction into CH2Cl2, evaporation gave the desired product.

후처리

  1. temperaturewas cooled to −75°
  2. customwas quenched with H2O
  3. washwashed with EtOAc
  4. extractionAfter acidification of the aqueous layer and extraction
  5. custominto CH2Cl2, evaporation

출처 및 근거

ORD 기록
ord-5b555b3220984de8a2f53c54beac1c55
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084609B2

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