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Dichloromethane → (4-(5-Bromopyridin-3-yl)phenyl)-(4-isopropylpiperazin-1-yl)-methanone

HRID 1970962
ノート
印刷プレビュー

反応式

HRID 1970962 の反応式
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Br:33][C:34]1[CH:35]=[N:36][CH:37]=[C:38](Br)[CH:39]=1.C(Cl)Cl>COCCOC.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]>[Br:33][C:34]1[CH:39]=[C:38]([C:15]2[CH:14]=[CH:13][C:12]([C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]3)=[O:11])=[CH:17][CH:16]=2)[CH:37]=[N:36][CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 68756040(4-Isopropyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

生成物 1

HCID 68733155(4-(5-Bromopyridin-3-yl)phenyl)-(4-isopropylpiperazin-1-yl)-methanone

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of (4-isopropylpiperazin-1-yl)-(4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl) phenyl)-methanone (step 1) (1.0 eq, 778 mg) in DME (4 ml) and 2M sodium carbonate solution (2 eq, 2.2 ml) is treated with 3,5-dibromopyridine (1 eq, 514 mg) followed by PdCl2(dppf).DCM (0.1 eq, 159 mg). The resulting mixture is heated using microwave radiation at 90° C. for 1 h. The mixture is extracted with DCM and the organic extracts are washed with water. The solvent is removed in vacuo and the crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane followed by 0-5% MeOH in DCM to afford the title compound [M+H]+=388/390.

後処理

  1. temperatureThe resulting mixture is heated
  2. customat 90° C.
  3. customfor 1 h
  4. extractionThe mixture is extracted with DCM
  5. washthe organic extracts are washed with water
  6. customThe solvent is removed in vacuo
  7. customthe crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-9f6f8b2af2c549b0a2f40c293c5ce09c
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431578B2

反応ノート

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