Potassium Fluoride → HCID 9840113, compound

HRID 1061735Notes

Reaction equation

HRID 1061735 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:15]3[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:13][CH:14]=2)O1.[F-].[K+].Cl[C:27]1[CH:36]=[CH:35][N:34]=[C:33]2[C:28]=1[CH:29]=[CH:30][C:31]([CH3:37])=[N:32]2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:37][C:31]1[N:32]=[C:33]2[C:28]([C:27]([C:9]3[CH:10]=[C:11]([C:15]4[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:12]=[CH:13][CH:14]=3)=[CH:36][CH:35]=[N:34]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 122663725-Chloro-2-methyl-1,8-naphthyridine

Product 1

HCID 9840113HCID 9840113, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

A mixture of tris(dibenzylideneacetone)dipalladium(0) (23 mg, 0.025 mmol), 3′-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (384 mg, 1.3 mmol), potassium fluoride (161 mg, 2.8 mmol) and 5-chloro-2-methyl-[1,8]naphthyridine (prepared as described by G. B. Barlin and W. L. Tan, Aust. J. Chem., 1984, 37, 1065-73; 150 mg, 0.84 mmol) was degassed by evacuating the reaction vessel and refilling it with nitrogen. Tri-tert-butylphosphine (0.50 ml of a 0.1 M solution in THF) and THF (15 ml) were added, and the mixture was degassed via three “freeze-thaw” cycles before stirring under nitrogen for 18 h. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with 10% to 100% EtOAc in dichloromethane, yielding 3′-(7-methyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile as a white solid (22 mg, 8%): δH (400 MHz, CDCl3) 2.83 (3H, s), 7.40 (1H, d, J 8.2), 7.45 (1H, d, J 4.3), 7.48-7.52 (1H, m), 7.57-7.60 (1H, m), 7.59 (1H, s), 7.67-7.71 (4H, m), 7.82 (1H, dd, J 0.8 and 7.8), 8.36 (1H, d, J 8.6), 9.11 (1H, d, J 4.3); m/z (ES+) 322 [MH]+.

Workup

  1. customwas degassed
  2. customby evacuating the reaction vessel
  3. additionTri-tert-butylphosphine (0.50 ml of a 0.1 M solution in THF) and THF (15 ml) were added
  4. customthe mixture was degassed via three “freeze-thaw” cycles
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography on silica gel
  7. washeluting with 10% to 100% EtOAc in dichloromethane

Sources & evidence

ORD record
ord-fc8906e3588145a09db24c284b541cae
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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