Sodium hydride → HCID 66966841、化合物

HRID 1435882ノート

反応式

HRID 1435882 の反応式
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][C:10]([C:12]([O:14]C)=O)=[CH:11][C:4]=12.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[NH4+].[Cl-]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(C)=O>[CH3:1][S:2][C:3]1[C:4]2[CH:11]=[C:10]3[N:9]([C:5]=2[N:6]=[CH:7][CH:8]=1)[CH2:19][CH2:20][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=[O:14]

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 76300Ethyl 4-bromobutyrateHCID 37818560Methyl 4-(methylsulfanyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

生成物 1

HCID 66966841HCID 66966841、化合物

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the compound of Step 4 (0.35 g, 1.6 mmol) in DMF (20 mL) at 0° C. was added NaH (1.2 eq.). After a period of 5 min., were added nBu4NI (0.10 g) and ethyl 4-bromobutyrate (0.40 mL). After a period of 1 h at room temperature, the reaction mixture was poured over saturated NH4Cl and EtOAc. The organic phase was separated, washed with H2O and dried over NaSO4. After evaporation the crude product was purified by flash chromatography. The bis ester was then dissolved in THF (7.0 mL) and a 1.06 M of THF solution of potassium tert-butoxide (2.2 mL) was added at 0° C. After a period of 1 h at room temperature, the reaction mixture was then poured over saturated NH4Cl and EtOAc. The organic phase was separated, dried over Na2SO4 and evaporated under reduced pressure to provide the title compound as a mixture of ethyl and methyl ester.

後処理

  1. waitAfter a period of 1 h at room temperature
  2. customThe organic phase was separated
  3. washwashed with H2O
  4. dry with materialdried over NaSO4
  5. customAfter evaporation the crude product
  6. customwas purified by flash chromatography
  7. dissolutionThe bis ester was then dissolved in THF (7.0 mL)
  8. additiona 1.06 M of THF solution of potassium tert-butoxide (2.2 mL) was added at 0° C
  9. waitAfter a period of 1 h at room temperature
  10. additionthe reaction mixture was then poured over saturated NH4Cl and EtOAc
  11. customThe organic phase was separated
  12. dry with materialdried over Na2SO4
  13. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-968f0cdf3ed048599bb56bec2743e027
出典データセット
uspto-grants-2009_11
特許番号
US07618979B2

反応ノート

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