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

HRID 1969857ノート

反応式

HRID 1969857 の反応式
[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

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 58382073HCID 58382073、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-99e8d60144f948eeb03b344b8079aa67
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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