2,4-Dichloro-6-(4-isopropoxyphenyl)pyridine → HCID 90117820, 화합물

HRID 523147

반응식

HRID 523147 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=1.[Br-].[S:20]1[CH:24]=[CH:23][N:22]=[C:21]1[Zn+]>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].C1COCC1>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=[C:2]([C:21]2[S:20][CH:24]=[CH:23][N:22]=2)[CH:7]=1

참가 물질

5

반응물 2

HCID 901180792,4-Dichloro-6-(4-isopropoxyphenyl)pyridineHCID 178419763HCID 178419763, 화합물2회

생성물 1

HCID 90117820HCID 90117820, 화합물수율 34%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매2회HCID 8028Tetrahydrofuran용매3회

실험 절차

To a dry 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (60 mg, 0.21 mmol) and Pd(dppf)Cl2 (8 mg, 10 μmol). The vial was sealed with a septum screw-cap and was then placed under N2 atmosphere. To the vial was added THF (0.5 mL), then thiazol-2-ylzinc(II) bromide in THF (0.5M, 0.53 mL, 0.27 mmol). The vial was placed in a 60° C. heating block with stirring for 2 hours. The vial was opened, and then charged with Pd(dppf)Cl2 (8 mg, 10 μmol). The vial was re-sealed and then placed under N2 atmosphere, and to the vial was added thiazol-2-ylzinc(II) bromide in THF (0.5M, 0.53 mL, 0.27 mmol). The vial was placed in a 60° C. heating block with stirring for 5 hours. The reaction solution was cooled to room temperature and then concentrated under a stream of N2. The resulting solid residue was subjected to silica gel chromatography to afford 2-(4-chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)thiazole as a white solid (24 mg, 34%).

후처리

  1. customTo a dry 2 dram vial equipped with a stir bar
  2. customThe vial was sealed with a septum
  3. customscrew-cap
  4. customwas placed in a 60° C.
  5. temperatureheating block
  6. customThe vial was re-sealed
  7. customwas placed in a 60° C.
  8. temperatureheating block
  9. stirringwith stirring for 5 hours
  10. concentrationconcentrated under a stream of N2

출처 및 근거

ORD 기록
ord-61f7cd78724448278b6c4f0140b562b7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334279B2

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