Ethyl Acetate → HCID 57898941, compound

HRID 910960Notes

Reaction equation

HRID 910960 reaction equation
[C:1]([CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH3:4])=[O:2].[CH3:25][C:26]1[N:27]=[C:28]([NH:31][C:32]2[CH:39]=[C:38]([O:40][C:41]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[CH:44]=[CH:43][CH:42]=3)[C:35]([CH:36]=O)=[CH:34][N:33]=2)[S:29][CH:30]=1.[C:51]([O:54][CH2:55]C)(=[O:53])[CH3:52]>C1COCC1>[CH3:25][C:26]1[N:27]=[C:28]([NH:31][C:32]2[N:33]=[CH:34][C:35](/[CH:36]=[CH:5]\[C:1]([O:3][CH3:4])=[O:2])=[C:38]([O:40][C:41]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[CH:44]=[CH:43][CH:42]=3)[CH:39]=2)[S:29][CH:30]=1.[CH3:25][C:26]1[N:27]=[C:28]([NH:31][C:32]2[N:33]=[CH:34][C:35](/[CH:36]=[CH:52]/[C:51]([O:54][CH3:55])=[O:53])=[C:38]([O:40][C:41]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[CH:44]=[CH:43][CH:42]=3)[CH:39]=2)[S:29][CH:30]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86634725HCID 86634725, compound

Product 2

HCID 57898941HCID 57898941, compoundYield 43%HCID 57898985(Z)-methyl 3-(6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)pyridin-3-yl)acrylateYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbomethoxymethylene triphenylphosphorane (0.517 g, 1.55 mmol) was added to a solution of 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinaldehyde (0.430 g, 1.19 mmol) in THF (5 mL). The reaction mixture was stirred for 2 hours and then concentrated, and the residue was purified via MPLC (Biotage), eluting with 1:1 hexane:ethyl acetate to provide (Z)-methyl 3-(6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)pyridin-3-yl)acrylate (0.072 g, 14% yield) and (E)-methyl 3-(6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)pyridin-3-yl)acrylate (0.216 g, 43% yield).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified via MPLC (Biotage)
  3. washeluting with 1:1 hexane

Sources & evidence

ORD record
ord-16b4b316764543cd8a21f05b85cb7b51
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…