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

HRID 1970962
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HRID 1970962 반응식
[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
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7

반응물 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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9f6f8b2af2c549b0a2f40c293c5ce09c
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431578B2

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