Triphenylphosphine → ((2-Methylthiazolo[5,4-b]pyridine-5-yl)methyl)triphenylphosphonium methanesulfonate

HRID 2259526Notes

Reaction equation

HRID 2259526 reaction equation
[CH3:1][S:2]([O:5][CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]([CH3:16])=[N:15][C:10]2=[CH:9][CH:8]=1)(=[O:4])=[O:3].[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:16][C:14]1[S:13][C:11]2[C:10]([N:15]=1)=[CH:9][CH:8]=[C:7]([CH2:6][P+:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[N:12]=2

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 220687645-(((Methanesulfonyl)oxy)methyl)-2-methylthiazolo[5,4-b]pyridine

Product 1

HCID 88435765((2-Methylthiazolo[5,4-b]pyridine-5-yl)methyl)triphenylphosphonium methanesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the mesylate of Step 7 (1.68 mmol) and triphenylphosphine (660 mg, 2.52 mmol) in 8 mL of anhyd. CH3CN was heated at reflux for 2 hr. The solvent was evaporated and the oil was swished in ether and the ether decanted twice. It was swished again in 25 mL ether over the weekend. The solvent was decanted to afford a very hygroscopic solid, which was dried under vacuum; yield: 732 mg, (84%).

Workup

  1. temperatureat reflux for 2 hr
  2. customThe solvent was evaporated
  3. customthe ether decanted twice
  4. customThe solvent was decanted
  5. customto afford a very hygroscopic solid, which
  6. customwas dried under vacuum

Sources & evidence

ORD record
ord-bc0b3cf2deff401ab837bfd5a66d9e49
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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