Water → 4-[(5-bromopyridin-2-yl)methoxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497382Notes

Reaction equation

HRID 1497382 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.[Br:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27]O)=[N:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][O:18][C:15]2[CH:16]=[CH:17][N:12]([C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[C:10]([CH3:11])[N:2]([CH3:1])[N:3]=4)[CH:8]=3)[C:13](=[O:19])[CH:14]=2)=[N:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5200169(5-Bromopyridin-2-yl)methanolHCID 1177986701-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 1177986934-[(5-bromopyridin-2-yl)methoxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (50 mg), (5-bromopyridin-2-yl)methanol (74 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. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with ethyl acetate, and recrystallized from ethanol-hexane to give the title compound (51 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained residue was washed with ethyl acetate
  6. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-d43a22a3e56249a49a7deea7b3d3308d
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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