Dimethylformamide → 5-(4-Fluorophenylethynyl)-pyridine-3-carbaldehyde

HRID 606879Notes

Reaction equation

HRID 606879 reaction equation
C([Mg]Cl)(C)C.[O:6]1CCC[CH2:7]1.Br[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:17]=1.CN(C)C=O>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]#[C:18][C:16]2[CH:17]=[C:12]([CH:7]=[O:6])[CH:13]=[N:14][CH:15]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 670476153-Bromo-5-(4-fluorophenylethynyl)-pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 860764705-(4-Fluorophenylethynyl)-pyridine-3-carbaldehydeYield 24%

Procedure

Prepare in a similar manner as described in EXAMPLE 90, using a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (2.99 mL, 5.98 mmol), 3-bromo-5-(4-fluorophenylethynyl)-pyridine (1.50 g, 5.43 mmol), (prepared essentially as described in EXAMPLE 96), and anhydrous N,N-dimethylformamide (1.99 g, 27.16 mmol) to give the title compound (0.29 g, 24%).

Workup

  1. customPrepare in a similar manner
  2. custom(prepared essentially

Sources & evidence

ORD record
ord-0fbfbc71b9504dfcb13a38ab6e4b5497
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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