Formic Acid → Methyl thieno[2,3-b]pyridine-5-carboxylate

HRID 2080023ノート

反応式

HRID 2080023 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:21]=[CH:20][S:19][C:8]2=[N:9][C:10]=1OS(C(F)(F)F)(=O)=O)=[O:4].C(O)=O.C(N(CC)C(C)C)(C)C.O>CN1CCCC1=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:21]=[CH:20][S:19][C:8]2=[N:9][CH:10]=1)=[O:4]

参加物

8

反応物 4

HCID 284Formic AcidHCID 962WaterHCID 81531DiisopropylethylamineHCID 58875349HCID 58875349、化合物

生成物 1

HCID 21817753Methyl thieno[2,3-b]pyridine-5-carboxylate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

6-Trifluoromethanesulfonyloxy-thieno[2,3-b]pyridine-5-carboxylic acid methyl ester described in Preparation Example T-9 (10 mg, 29 μmol), tetrakis(triphenylphosphine)palladium(0) (3.4 mg, 2.9 μmol), formic acid (1.7 μl, 44 μmol) and N,N-diisopropylethylamine (15 μl, 87 μmol) were dissolved in 1-methyl-2-pyrrolidone (0.5 mL), and the mixture was stirred for 1.5 hours at 100° C. The reaction mixture was cooled to room temperature, water and ethyl acetate were added, the organic layer was partitioned, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (7 mg, quantitatively) was obtained as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was partitioned
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-4b085073c61944209e6c2c77853628f9
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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