Dichloromethane → HCID 58443272, compound

HRID 1630738Notes

Reaction equation

HRID 1630738 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:17]2[CH:18]=[N:19][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:21][CH:22]=2)[C:13]([F:16])=[N:14][CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[N+]1([O-])CCOCC1.C(Cl)Cl>C1COCC1.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:16][C:13]1[C:12]([C:17]2[CH:18]=[N:19][C:20]([O:23][CH2:24][C:25]([F:28])([F:26])[F:27])=[CH:21][CH:22]=2)=[CH:11][C:10]([CH:9]=[O:8])=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 2724141Tetrabutylammonium FluorideHCID 67417570HCID 67417570, compound

Product 1

HCID 58443272HCID 58443272, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-((tert-Butyldimethylsilyloxy)methyl)-2-fluoro-3-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)pyridine (0.204 g, 0.490 mmol) was placed into a flask with 5.0 mL of tetra-butylammonium fluoride in THF and stirred for 4 h. The reaction was then quenched by adding water (5 mL) and extracting with EtOAc (3×5 mL). The combined organic layers were then washed with brine (1×5 mL), dried (MgSO4), filtered, and concentrated. The resulting crude oil (0.145 g, 0.480 mmol) was then placed into a flame-dried flask, and to the reaction mixture was added N-methylmorpholine N-oxide (0.169 g, 1.44 mmol), 4 Å molecular sieves (10 mg), and CH2Cl2 (1.0 mL). Tetrapropylammonium perruthenate (8.43 mg, 0.024 mmol) was then added, and the suspension was stirred at rt overnight. The reaction mixture was worked-up by filtering through Celite® and concentrating the filtrate to give 6-fluoro-5-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)nicotinaldehyde.

Workup

  1. customThe reaction was then quenched
  2. additionby adding water (5 mL)
  3. extractionextracting with EtOAc (3×5 mL)
  4. washThe combined organic layers were then washed with brine (1×5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringthe suspension was stirred at rt overnight
  9. filtrationby filtering through Celite®
  10. concentrationconcentrating the filtrate

Sources & evidence

ORD record
ord-bda1b59046fa4f7381cc15bd821c587c
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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