Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 16661153, compound

HRID 1426144Notes

Reaction equation

HRID 1426144 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:11][CH:12]=[C:13]([CH:16]=1)[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:47])[CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:16]=[C:13](/[CH:14]=[CH:27]/[C:26]([O:25][CH3:24])=[O:47])[CH:12]=[N:11][C:10]=1[NH:17][C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester2×HCID 16661007HCID 16661007, compound

Product 1

HCID 16661153HCID 16661153, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 25 mL round-bottomed flask was charged with 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (500 mg, 1.54 mmol) and THF (10 mL). Methyl(triphenylphosphoranylidene)acetate (668 mg, 2.00 mmol) was added and the reaction was stirred at room temperature for 1 hour. An additional 668 mg of methyl(triphenylphosphoranylidene)acetate was added and the reaction was stirred overnight. The solids were filtered off and the filtrate was purified on a silica gel column (1:1 EtOAc:Hexanes) to afford (E)-methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)acrylate (450 mg, 76.8% yield) as a yellow foam. 1H NMR (CDCl3) 8.69 (s, 1H), 8.07 (d, 1H), 7.65 (d, 1H), 7.42 (m, 5H), 7.25 (m, 1H), 6.45 (m, 1H), 6.30 (d, 1H), 5.15 (s, 2H), 3.81 (s, 3H), 2.33 (s, 3H). Mass spectrum (apci) m/z=382.0 (M+H).

Workup

  1. stirringthe reaction was stirred overnight
  2. filtrationThe solids were filtered off
  3. customthe filtrate was purified on a silica gel column (1:1 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-f5ea4149ff1b4dfeb47278f1406e4b9e
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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