Triphenylphosphine → HCID 117816753, compound

HRID 1497405Notes

Reaction equation

HRID 1497405 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]3=[O:19])=[CH:8]2)=[N:3]1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]O)=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:27][C:24]4[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=4)=[CH:14][C:13]3=[O:19])=[CH:8]2)=[N:3]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 680224-Fluorobenzylic alcoholHCID 1177986701-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 117816753HCID 117816753, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (500 mg), (4-fluorophenyl)methanol (494 mg) and triphenylphosphine (1.54 g) in tetrahydrofuran (40 ml) was added bis(2-methoxyethyl)azodicarboxylate (1.38 g) at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (712 mg).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-aad3f2214f684e66bd9655c063f9119c
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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