Dichloromethane → 2-(4,6-Dichloropyridin-2-yl)thiazole

HRID 523140

반응식

HRID 523140 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[Br-].[S:11]1[CH:15]=[CH:14][N:13]=[C:12]1[Zn+].C1COCC1.C(Cl)Cl>O.[Na+].[Cl-].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].CO>[Cl:8][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([C:12]2[S:11][CH:15]=[CH:14][N:13]=2)[CH:7]=1

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 27665Pyridine, 2,4,6-trichloro-HCID 178419763HCID 178419763, 화합물

생성물 1

HCID 901181032-(4,6-Dichloropyridin-2-yl)thiazole수율 46%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 887Methanol용매HCID 962Water용매HCID 5234Sodium Chloride용매

실험 절차

To a 15 mL vial equipped with a stir bar was added 2,4,6-trichloropyridine (182 mg, 1.00 mmol) and Pd(dppf)Cl2 (73.2 mg, 0.100 mmol). The vial was sealed with a septum screwcap and was then placed under N2 atmosphere. To the vial was added thiazol-2-ylzinc(II) bromide in THF (8.00 mL, 4.00 mmol). The vial was placed in a 60° C. heating block with stirring for 3 h. The reaction mixture was transfered to a separatory funnel and diluted with water (25 mL) and sat. aq. NaCl (“brine”, 25 mL). The mixture was extracted with EtOAc:Et2O (40 mL:20 mL). The organic phase was washed with brine (25 mL); dried over MgSO4; filtered; then concentrated in vacuo to afford an orange solid. This material was subjected to silica gel chromatography (CH2Cl2:MeOH, 100:0 to 99:1) to afford 2-(4,6-dichloropyridin-2-yl)thiazole as a white solid (231 mg, 46%). 1H-NMR (400 MHz, CDCl3) δ 8.16 (d, J=1.8 Hz, 1H), 7.95 (d, J=3.3 Hz, 1H), 7.52 (d, J=3.0 Hz, 1H), 7.37 (d, J=1.8 Hz, 1H).

후처리

  1. customTo a 15 mL vial equipped with a stir bar
  2. customThe vial was sealed with a septum screwcap
  3. customwas placed in a 60° C.
  4. temperatureheating block
  5. customThe reaction mixture was transfered to a separatory funnel
  6. extractionThe mixture was extracted with EtOAc
  7. washThe organic phase was washed with brine (25 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationthen concentrated in vacuo
  11. customto afford an orange solid

출처 및 근거

ORD 기록
ord-96a790dea285473b9f8e7aad7f33b977
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334279B2

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