Sulfuric Acid → ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

HRID 733743

반응식

HRID 733743 반응식
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10](CC3C=CC(OC)=CC=3)[C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1.S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1

참가 물질

7

반응물 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 57840887Ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

생성물 1

HCID 57840913ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate수율 76.7%

시약·촉매·용매 3

HCID 1118Sulfuric Acid촉매HCID 6422Trifluoroacetic acid용매HCID 7519Anisole용매

실험 절차

A solution of ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (1.00 g) in TFA (5 ml) and anisole (0.92 ml) was stirred at room temperature for 2.5 h. Sulphuric acid (5 drops) was added to the reaction mixture and stirring continued for 2 h then sulphuric acid (2 ml) was added and the reaction mixture stirred for 24 h at room temperature. The solution was added to saturated sodium bicarbonate at 0° C. and extracted with ethyl acetate. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a brown solid (0.50 g).

후처리

  1. stirringthe reaction mixture stirred for 24 h at room temperature
  2. extractionextracted with ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-5c6b7da5433c4a8c8cc6d86145654fa3
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589206B2

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