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

HRID 8246

반응식

HRID 8246 반응식
[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]

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-8a78da593f264a14928d76c76ca79538
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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