Acetone → (2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylaldehyde

HRID 2390651Notes

Reaction equation

HRID 2390651 reaction equation
C([O:3][CH:4](OCC)/[CH:5]=[CH:6]/[C:7]1[C:8]2[S:16][CH:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[C:9]=2[C:10]([NH2:13])=[N:11][CH:12]=1)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>O>[NH2:13][C:10]1[C:9]2[C:14]([C:17]3[CH:18]=[CH:19][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:21][CH:22]=3)=[CH:15][S:16][C:8]=2[C:7](/[CH:6]=[CH:5]/[CH:4]=[O:3])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 184508607-[(1e)-3,3-Diethoxy-1-propenyl]-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

Product 1

HCID 18450607(2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylaldehydeYield 106%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 360A (170 mg, 0.38 mmol), p-toluenesulfonic acid (10 mg), acetone (9 mL), and water (1 mL) was stirred for 1.25 hours and concentrated. The residue partioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic layer was dried (MgSO4), filtered, and concentrated to provide the desired product (150 mg). 1H NMR (DMSO-d6, 400 MHz) δ 9.66 (d, 1H), 8.32 (s, 1H), 7.89 (d, 1H), 7.68 (s, 1H), 7.47 (m, 4H), 7.20 (t, 1H), 7.14 (m, 4H), 6.65 (dd, 1H); MS m/e 373.3 (M+H)+, 371.1 (M−H)−.

Workup

  1. concentrationconcentrated
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ad44f4d504694ca7af4172caf118e17e
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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