Tetrahydrofuran → HCID 86690766, compound

HRID 1471744Notes

Reaction equation

HRID 1471744 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[O:5]1[CH2:9][CH2:8][O:7][CH:6]1[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[N:13]=[CH:12][C:11]=1[O:18][CH2:19][C:20]1[C:21]([C:26]#N)=[N:22][CH:23]=[CH:24][CH:25]=1.C1C[O:31]CC1>>[O:7]1[CH2:8][CH2:9][O:5][CH:6]1[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[N:13]=[CH:12][C:11]=1[O:18][CH2:19][C:20]1[C:21]([C:26](=[O:31])[CH2:1][CH3:2])=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 86690779HCID 86690779, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86690766HCID 86690766, compoundYield 58%

Procedure

Ethylmagnesium bromide (3M/ether, 1.53 mL, 4.60 mmol, 1.5 eq.) was added to a stirred solution of 3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinonitrile (960 mg, 3.07 mmol, 1 eq.) in THF (15.0 mL) at −78° C. After addition, the reaction mixture was allowed to warm to rt and quenched with aqueous citric acid solution. The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with NaHCO3(sat) solution and brine, dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 1-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-1-one (611 mg, 58%) as a colorless oil. LRMS (M+H+) m/z 345.1.

Workup

  1. additionAfter addition
  2. customquenched with aqueous citric acid solution
  3. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
  4. washThe combined organic layers were washed with NaHCO3(sat) solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified on silica gel using
  8. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-2f2ad0f700ab45329b16e203049a46b9
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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