Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)acrylate

HRID 335096Notes

Reaction equation

HRID 335096 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:15]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:11]([CH:12]=O)=[CH:10][N:9]=2)[S:5][CH:6]=1.[CH3:23][O:24][C:25](=[O:46])[CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:9]=[CH:10][C:11](/[CH:12]=[CH:26]/[C:25]([O:24][CH3:23])=[O:46])=[CH:14][C:15]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester2×HCID 866314726-(4-Methylthiazol-2-ylamino)-5-phenoxynicotinaldehyde

Product 1

HCID 86631473(E)-methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)acrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of mL 6-(4-methylthiazol-2-ylamino)-5-phenoxynicotinaldehyde (311 mg, 1.00 mmol) and THF (10 mL) was added methyl(triphenylphosphoranylidene)acetate (500 mg, 1.5 mmol) and the reaction mixture was stirred at room temperature. After 4 hours, additional methyl(triphenylphosphoranylidene)acetate (500 mg, 1.5 mmol) was added and the reaction mixture was stirred overnight. Filtered, concentrated the filtrate, and purified by silica gel chromatography (1:1 EtOAc in hexanes) to afford (E)-methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)acrylate.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. filtrationFiltered
  3. concentrationconcentrated the filtrate
  4. custompurified by silica gel chromatography (1:1 EtOAc in hexanes)

Sources & evidence

ORD record
ord-bb57f7d71909457ab7b3113c1266a991
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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