Dichloromethane → Methyl 2 inverted exclamation mark-Oxo-1 inverted exclamation mark-[[2-(trimethylsilyl)ethoxy]methyl]-1 inverted exclamation mark,2 inverted exclamation mark,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3 inverted exclamation mark-pyrrolo[2,3-b]pyridine]-3-carboxylate

HRID 588723노트

반응식

HRID 588723 반응식
Br[C:2]1[CH:3]=[C:4]2[CH2:27][C:9]3([C:17]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[N:11]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:10]3=[O:26])[CH2:8][C:5]2=[N:6][CH:7]=1.[CH2:28](Cl)Cl.[C:31]([O-:34])(=[O:33])C.[Na+].[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]>[O:26]=[C:10]1[N:11]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:17]2[C:9]21[CH2:8][C:5]1=[N:6][CH:7]=[C:2]([C:31]([O:34][CH3:28])=[O:33])[CH:3]=[C:4]1[CH2:27]2

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 68749705HCID 68749705, 화합물2회HCID 178418416HCID 178418416, 화합물

생성물 1

HCID 131734435Methyl 2 inverted exclamation mark-Oxo-1 inverted exclamation mark-[[2-(trimethylsilyl)ethoxy]methyl]-1 inverted exclamation mark,2 inverted exclamation mark,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3 inverted exclamation mark-pyrrolo[2,3-b]pyridine]-3-carboxylate

시약·촉매·용매 2

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

반응 조건

온도
85 °C

실험 절차

A mixture of 3-bromo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (described in Intermediate 2) (22.0 g, 49.3 mmol), PdCl2(dppf).CH2Cl2 (2.012 g, 2.46 mmol), and sodium acetate (8.1 g, 99 mmol) in MeOH (150 mL) was pressurized to 300 psi of carbon monoxide and then heated at 85° C. for 72 h. The reaction mixture was allowed to cool then concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of heptane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=426.1 (M+1).

후처리

  1. temperatureto cool
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with a gradient of heptane

출처 및 근거

ORD 기록
ord-fbfd66fc901344bab79d4f21f480d7a7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227972B2

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