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 588723ノート

反応式

HRID 588723 の反応式
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

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 68749705HCID 68749705、化合物2 回HCID 178418416HCID 178418416、化合物

生成物 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

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

反応条件

温度
85 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-fbfd66fc901344bab79d4f21f480d7a7
出典データセット
uspto-grants-2016_01
特許番号
US09227972B2

反応ノート

読み込み中…