Triphenylphosphine → 6-(3,5-difluorophenyl)-2-[3-(5-methylpyridin-2-yl)benzyl]-2H-pyridazin-3-one

HRID 1408389Notes

Reaction equation

HRID 1408389 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:23]=[C:24]([CH2:28]O)[CH:25]=[CH:26][CH:27]=2)=[N:20][CH:21]=1.[F:30][C:31]1[CH:32]=[C:33]([C:38]2[CH:39]=[CH:40][C:41](=[O:44])[NH:42][N:43]=2)[CH:34]=[C:35]([F:37])[CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:30][C:31]1[CH:32]=[C:33]([C:38]2[CH:39]=[CH:40][C:41](=[O:44])[N:42]([CH2:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:19]4[CH:18]=[CH:17][C:16]([CH3:15])=[CH:21][N:20]=4)[CH:23]=3)[N:43]=2)[CH:34]=[C:35]([F:37])[CH:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 25241749HCID 25241749, compoundHCID 56604357(3-(5-Methylpyridin-2-yl)phenyl)methanol

Product 1

HCID 594848946-(3,5-difluorophenyl)-2-[3-(5-methylpyridin-2-yl)benzyl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.2 134 mg (0.66 mmol) of diisopropyl azodicarboxylate are added to a solution of 88 mg (0.44 mmol) of [3-(5-methylpyridin-2-yl)phenyl]methanol, 138 mg (0.66 mmol) of 6-(3,5-difluorophenyl)-2H-pyridazin-3-one and 174 mg (0.66 mmol) of triphenylphosphine in 3.5 ml of THF. The reaction mixture is stirred at room temperature for 18 hours. The mixture is evaporated, and the residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent: 6-(3,5-difluorophenyl)-2-[3-(5-methylpyridin-2-yl)benzyl]-2H-pyridazin-3-one (“A9”) as colourless crystals; ESI 390.

Workup

  1. customThe mixture is evaporated
  2. customthe residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-d9f3a906aada457db5444dbcb73fdcff
Source dataset
uspto-grants-2014_12
Patent number
US08921357B2

Reaction notes

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