Ethanol → HCID 86684761, compound

HRID 1408893Notes

Reaction equation

HRID 1408893 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([OH:13])[CH2:11][OH:12])[CH:5]=[N:6][C:7]=1Cl.CCO.CC1(C)C(C)(C)OB([C:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH:26]=2)O1>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:34]([O:33][C:31]([N:28]1[CH2:29][CH2:30][C:25]([C:7]2[C:2]([Cl:1])=[CH:3][C:4]([CH2:9][CH:10]([OH:13])[CH2:11][OH:12])=[CH:5][N:6]=2)=[CH:26][CH2:27]1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

7

Reactant 3

HCID 702EthanolHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 86684760HCID 86684760, compound

Product 1

HCID 86684761HCID 86684761, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-(5,6-dichloropyridin-3-yl)propane-1,2-diol 59 (255 mg, 1.148 mmol) in THF (1.8 ml)-EtOH (0.7 ml)-3M K2CO3 aq. (0.842 ml, 2.53 mmol) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2 H)-carboxylate 33 (391 mg, 1.263 mmol) and PdCl2(PPh3)2 (24.18 mg, 0.034 mmol) at room temperature under N2. The mixture was stirred at 85° C. for 1.5 hr. The reaction mixture was diluted with H2O, then extracted with EtOAc (3×10 mL). The organic layers were combined and washed with brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was added to a silica gel chromatography column and was eluted with CHCl3/MeOH (10:1) Collected fractions were evaporated to afford 60 (404 mg 1.095 mmol 95%) as a yellow oil.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe crude product was added to a silica gel chromatography column
  7. washwas eluted with CHCl3/MeOH (10:1)
  8. customCollected fractions
  9. customwere evaporated

Sources & evidence

ORD record
ord-f47637d267af4616b41a147fe7a72c45
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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