Triphenylphosphine → HCID 89689924, compound

HRID 2203022Notes

Reaction equation

HRID 2203022 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]4=[O:19])=[CH:8][N:7]3[C:20]=2[CH3:21])[CH2:3][CH2:2]1.[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]O)=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][O:18][C:15]2[CH:16]=[CH:17][N:12]([C:9]3[CH:10]=[CH:11][C:6]4[N:7]([C:20]([CH3:21])=[C:4]([CH:1]5[CH2:3][CH2:2]5)[N:5]=4)[CH:8]=3)[C:13](=[O:19])[CH:14]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 701194-Bromobenzyl alcoholHCID 896902811-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 89689924HCID 89689924, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (500 mg) in THF (5 ml) were added p-bromobenzyl alcohol (332 mg), (E)-bis(2-methoxyethyl)diazene-1,2-dicarboxylate (541 mg) and triphenylphosphine (606 mg), and the mixture was stirred at room temperature for 16 h. The mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (EtOAc/MeOH), followed by crystallization from hot EtOAc to give the title compound (502 mg) as white crystals.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel column chromatography (EtOAc/MeOH)
  6. customfollowed by crystallization from hot EtOAc

Sources & evidence

ORD record
ord-4174644bc54c42d98ab6730bcba1fbae
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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