Tetrabutylammonium Fluoride → Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1969857노트

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HRID 1969857 반응식
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([Si](C(C)C)(C(C)C)C(C)C)[CH:14]=[CH:15][C:3]=12.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[CH:15][C:3]=12

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 58382073HCID 58382073, 화합물

생성물 1

HCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of ethyl 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (4.30 g, 11.3 mmol) in THF (57 mL) at about 0° C. was added TBAF (1.0 M in THF, 12.6 mL, 12.6 mmol) dropwise and the reaction mixture was stirred at about 0° C. for about 1 h. The reaction was warmed to room temperature and stirred for about 30 min. The solvent was removed under reduced pressure and the resulting oil was partitioned between EtOAc and brine (100 mL each). The organic layer was dried over anhydrous Na2SO4, filtered and concd under reduced pressure. The residue was triturated with DCM and filtered to give ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.32 g, 52%) as an off white solid: LC/MS (Table 1, Method b) Rt=2.07 min; MS m/z: 225 (M+H)+.

후처리

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred for about 30 min
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting oil was partitioned between EtOAc and brine (100 mL each)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe residue was triturated with DCM
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-99e8d60144f948eeb03b344b8079aa67
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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