Triphenylphosphine → 4-[(3-chlorobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497373Notes

Reaction equation

HRID 1497373 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.[Cl:20][C:21]1[CH:22]=[C:23]([CH2:27]O)[CH:24]=[CH:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[CH2:27][O:18][C:15]1[CH:16]=[CH:17][N:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[C:10]([CH3:11])[N:2]([CH3:1])[N:3]=3)[CH:8]=2)[C:13](=[O:19])[CH:14]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 701173-Chlorobenzyl alcoholHCID 1177986701-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 1177986634-[(3-chlorobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 48.4%

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 (50 mg), (3-chlorophenyl)methanol (56 mg) and triphenylphosphine (154 mg) in tetrahydrofuran (5 ml) was added bis(2-methoxyethyl)azodicarboxylate (138 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hr. 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 (36 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-401684d8cc1046f98b2c266e63cb66dc
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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