3-Pyridinemethanol → HCID 22046419, compound

HRID 1821771Notes

Reaction equation

HRID 1821771 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[CH:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1.C(OCC)(=O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([O:19][CH2:18][C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 3

HCID 75103-PyridinemethanolHCID 677672,5-DifluoronitrobenzeneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 22046419HCID 22046419, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, cooled (about 0° C.) solution of 1,4-Difluoro-2-nitro-benzene (3.0 mmol) and 3-pyridylcarbinol (3.1 mmol) in tetrahydrofuran (8 mL) was added lithium bis(trimethylsilyl)amide (3.2 mmol; 3.2 mL of a 1.0 M solution in tetrahydrofuran). After stirring for 12 hours, the reaction was diluted with 30 mL of ethyl acetate and washed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL), then dried (MgSO4) and filtered. The filtered solution was concentrated under reduced pressure to provide the desired crude product.

Workup

  1. washwashed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-922ed7d963b244b9a6f1d494a9353927
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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