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

HRID 1497386
Notes
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Reaction equation

HRID 1497386 reaction equation
[CH:1]1([N:4]2[C:12]([CH3:13])=[C:11]3[C:6]([CH:7]=[CH:8][C:9]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])=[CH:10]3)=[N:5]2)[CH2:3][CH2:2]1.[Br:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29]O)=[N:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][O:20][C:17]2[CH:18]=[CH:19][N:14]([C:9]3[CH:8]=[CH:7][C:6]4[C:11](=[C:12]([CH3:13])[N:4]([CH:1]5[CH2:2][CH2:3]5)[N:5]=4)[CH:10]=3)[C:15](=[O:21])[CH:16]=2)=[N:27][CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5200169(5-Bromopyridin-2-yl)methanolHCID 1177986831-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 1177986734-[(5-bromopyridin-2-yl)methoxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 42.4%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (50 mg), (5-bromopyridin-2-yl)methanol (67 mg) and triphenylphosphine (140 mg) in tetrahydrofuran (6 ml) was added bis(2-methoxyethyl)azodicarboxylate (125 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 purified by silica gel column chromatography (hexane/ethyl acetate/methanol) and recrystallized from ethanol-hexane to give the title compound (34 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. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)
  6. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-d8f6d766de0a45edbfcdf3a61d8ca425
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199963B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes