Dimethylformamide → 4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine-2-carbonitrile

HRID 1959600노트

반응식

HRID 1959600 반응식
Cl[C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6]([Cl:16])[CH:5]=[CH:4][N:3]=1.[CH3:17][N:18](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.[Zn].C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:16][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:17]#[N:18])[C:7]=1[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1

참가 물질

8

반응물 2

HCID 6228DimethylformamideHCID 86645362HCID 86645362, 화합물

생성물 1

HCID 670775644-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine-2-carbonitrile

시약·촉매·용매 5

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11192Zinc Acetate촉매HCID 23994Zinc촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 962Water용매

반응 조건

온도
95 °C

실험 절차

2,4-Dichloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (455 mg. 1.74 mmol) was dissolved in a mixture of DMF (3 mL) and water (30 μL). The following reagents were added subsequently: zinc cyanide (112 mg. 0.95 mmol), zinc dust (9.1 mg. 139 μmol), zinc acetate (25.5 mg. 139 μmol). 1,1′-bis(diphenylphosphino)ferrocene (58 mg. 104 μmol) and tris(dibenzylideneacetone)palladium (0). The reaction mixture was degassed two times and afterwards heated at 95° C. for 4 h. The solvents were removed in vacuo and the residue was pardoned between water (20 mL) and EtOAc (20 mL) and extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine and dried over Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 10:1→5:1) to give the title compound. MS (m/z): 253.0 [M+H+].

후처리

  1. additionThe following reagents were added subsequently
  2. customThe reaction mixture was degassed two times
  3. customThe solvents were removed in vacuo
  4. extractionextracted with EtOAc (3×20 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 10:1→5:1)

출처 및 근거

ORD 기록
ord-7cb16a4656344b03b88ce7122d259da3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410134B2

반응 노트

불러오는 중…