Thionyl Chloride → 3-(4-Fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

HRID 1465952ノート

反応式

HRID 1465952 の反応式
[CH3:1][O:2][C:3]([CH:5]1[N:10](CC2C=CC(OC)=CC=2OC)[CH2:9][C:8]2[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][S:24][C:7]=2[C:6]1=[O:32])=[O:4].S(Cl)(Cl)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:10]=[CH:9][C:8]2[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][S:24][C:7]=2[C:6]=1[OH:32])=[O:4]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 672335175-(2,4-Dimethoxy-benzyl)3-(4-fluoro-phenyl)-7-oxo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

生成物 1

HCID 672328323-(4-Fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester収率 61.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5-(2,4-dimethoxy-benzyl)-3-(4-fluoro-phenyl)-7-oxo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester (0.39 g, 0.86 mmol), example 31-e, was dissolved in 6 mL of anhydrous dichloromethane. To the solution was added 93.7 μL of thionyl chloride, and the reaction mixture was stirred for 5 hours. The solution was filtered on a fine glass frit filter to collect a white solid precipitate. The solid was washed twice with cold dichloromethane and then partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to produce 0.16 g of a white solid. MS: (+) m/z 304.0 (M+1)

後処理

  1. filtrationThe solution was filtered on a fine glass frit
  2. filtrationfilter
  3. customto collect a white solid precipitate
  4. washThe solid was washed twice with cold dichloromethane
  5. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  6. washThe organic fraction was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-f646457a525e49aba8c65efac2322d41
出典データセット
uspto-grants-2015_04
特許番号
US09000006B2

反応ノート

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