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

HRID 733743

反応式

HRID 733743 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1118Sulfuric Acid触媒HCID 6422Trifluoroacetic acid溶媒HCID 7519Anisole溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5c6b7da5433c4a8c8cc6d86145654fa3
出典データセット
uspto-grants-2009_09
特許番号
US07589206B2

関連ノート

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