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

HRID 1270880Notes

Reaction equation

HRID 1270880 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-08619c58280e4549a011013b44adb1fe
Source dataset
uspto-grants-2007_04
Patent number
US07202363B2

Reaction notes

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