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

HRID 2080023노트

반응식

HRID 2080023 반응식
[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]

참가 물질

8

반응물 4

HCID 284Formic AcidHCID 962WaterHCID 81531DiisopropylethylamineHCID 58875349HCID 58875349, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4b085073c61944209e6c2c77853628f9
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

반응 노트

불러오는 중…