Carbon Dioxide → 2-((tert-Butyldimethylsilyloxy)methyl)-1-methyl-1H-indole-5-carboxylic acid

HRID 1481751노트

반응식

HRID 1481751 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:5]2.[Li]CCCC.[C:26](=[O:28])=[O:27]>C1COCC1>[Si:14]([O:13][CH2:12][C:6]1[N:7]([CH3:11])[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([C:26]([OH:28])=[O:27])=[CH:10][CH:9]=2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 712845855-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indoleHCID 178418339Butyllithium

생성물 1

HCID 712850522-((tert-Butyldimethylsilyloxy)methyl)-1-methyl-1H-indole-5-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indole (5.32 g, 15.0 mmol), prepared according to procedure described in Example 39, Step 3, in THF (30 mL) was added n-BuLi (2.5 M solution in hexanes, 7.30 mL, 18.25 mmol, 1.2 eq) at −78° C. dropwise. The mixture was stirred for 30 min at −78° C. before dry CO2 (g) was bubbled into reaction for 10 min. The reaction was quenched with saturated aqueous NH4Cl then extracted by CH2Cl2 (3×50 mL). The combined organic layers were dried over Na2SO4 then concentrated under reduced pressure to give the title compound (4.80 g, ca. 15.0 mmol) in quantitative yield. The acid was carried over to next step without further purification.

후처리

  1. customwas bubbled into reaction for 10 min
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionthen extracted by CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1a85251999fd460db08b0ffa853b9fee
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409905B2

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