Di-3-pyridinylmethanone → HCID 11632460, compound

HRID 1360119Notes

Reaction equation

HRID 1360119 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:8])[CH:2]=1.[F:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][N:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]2=[O:27])=[CH:18][CH:17]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:15][C:16]1[CH:29]=[CH:28][C:19]([CH:20]([N:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]2=[O:27])[C:7]([OH:8])([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 298471Di-3-pyridinylmethanoneHCID 2733832Lithium HexamethyldisilazideHCID 457961441-[(4-Fluorophenyl)methyl]pyridin-2(1H)-one

Product 1

HCID 11632460HCID 11632460, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of dipyridin-3-ylmethanone (1 g, 5.9 mmol) and 1-(4-fluorobenzyl)pyridin-2(1H)-one (1 g, 4.9 mmol) in THF (50 mL) was cooled to −78 C. To the resulting white suspension was added in a dropwise manner, LiHMDS (1M in THF, 6 mL). The resulting cream suspension was stirred for 30 min then allowed to warm up gradually to −30 C over 1 h. The reaction mixture was quenched with saturated NaHCO3 and then it was extracted once with ether and once with ethyl acetate. The combined extracts were dried over Na2SO4 and concentrated. The resulting yellow oil was purified by normal phase Gilson chromatography eluting with 98% DCM, 2% methanol. The product was isolated as a white solid.

Workup

  1. temperatureto warm up gradually to −30 C over 1 h
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. extractionit was extracted once with ether and once with ethyl acetate
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting yellow oil was purified by normal phase Gilson chromatography
  7. washeluting with 98% DCM, 2% methanol
  8. customThe product was isolated as a white solid

Sources & evidence

ORD record
ord-8459fdc5a8784574aab0a4de9e4da5c7
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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