Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetate

HRID 1036633ノート

反応式

HRID 1036633 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:28][CH:29]=O)[CH2:13][N:14]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH:28]=[CH:29][C:15]3[N:14]([C:18]4[N:19]=[CH:20][CH:21]=[CH:22][C:17]=4[C:16]=3[CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86655915Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

生成物 1

HCID 86655916methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetate収率 70.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate (0.69 g, 1.6 mmol) in toluene (50 mL) was added PPTS (0.41 g, 1.6 mmol, 1.2 equiv.). After a period of 10 h at 90° C., the reaction mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by combiflash (10% ethyl acetate in hexane to 100% ethyl acetate) to give 469 mg of the title compound.

後処理

  1. customthe reaction mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by combiflash (10% ethyl acetate in hexane to 100% ethyl acetate)

出典と根拠

ORDレコード
ord-e39ee06a536a4ac7a2e2f9cf3dfeb2c7
出典データセット
uspto-grants-2013_10
特許番号
US08546422B2

反応ノート

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