Dichloromethane → methyl 4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylate

HRID 8246

反応式

HRID 8246 の反応式
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH2:6](Cl)Cl.BrC1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[C:20]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:23][N:22]2[CH2:31][CH2:32][CH2:33][C:21]=12.[C]=O>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:6][O:3][C:1]([C:2]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[C:20]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:23][N:22]2[CH2:31][CH2:32][CH2:33][C:21]=12)=[O:4]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 101350276-bromo-4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolineHCID 178418416HCID 178418416、化合物

生成物 1

HCID 10133736methyl 4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylate

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 887Methanol溶媒

実験手順

To a mixture of sodium acetate (0.84 g, 10.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II):CH2Cl2 (42 mg, 0.05 mmol) in methanol (40 mL) is added 6-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (1.0 g, 2.56 mmol). The mixture is heated at 90° C. under 68 psi carbon monoxide for 24 h. The mixture is cooled, filtered, and concentrated in vacuo. The product is partitioned between ethyl acetate and: water. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on SiO2 (dichloromethane to 2% methanol/dichloromethane) to yield a solid, 918 mg (97%).

後処理

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe product is partitioned between ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on SiO2 (dichloromethane to 2% methanol/dichloromethane)
  8. customto yield a solid, 918 mg (97%)

出典と根拠

ORDレコード
ord-8a78da593f264a14928d76c76ca79538
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

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