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

HRID 2390655Notes

Reaction equation

HRID 2390655 reaction equation
[Br:1][C:2]1[C:6]2[C:7]([NH2:20])=[N:8][CH:9]=[C:10](/[CH:11]=[CH:12]/[CH:13](OCC)[O:14]CC)[C:5]=2[S:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>O>[NH2:20][C:7]1[C:6]2[C:2]([Br:1])=[CH:3][S:4][C:5]=2[C:10](/[CH:11]=[CH:12]/[CH:13]=[O:14])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 184507743-Bromo-7-[(1e)-3,3-diethoxy-1-propenyl]thieno[3,2-c]pyridin-4-amine

Product 1

HCID 18450636(2e)-3-(4-Amino-3-bromothieno[3,2-c]pyridin-7-yl)acrylaldehydeYield 164.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 176A (200 mg, 0.56 mmol), p-toluenesulfonic acid (10 mg), acetone (10 mL), and water (1 mL) at ambient temperature was stirred for 16 hours. The mixture was concentrated and washed with sodium bicarbonate (12 mL). The aqueous layer was extracted with dichloromethane/methanol (9:1). The combined organic extracts were concentrated to provide the desired product (160 mg, 0.92 mmol). Reverse phase HPLC (5% to 95% acetonitrile over 25 minutes, 1 mL/min, 254 nm, hypersil HS 100 Å, C18, 5 μm, 250×4.6 column) Rt=15.5 min.

Workup

  1. concentrationThe mixture was concentrated
  2. washwashed with sodium bicarbonate (12 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane/methanol (9:1)
  4. concentrationThe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-090f99074525494b9ebc5022f134f690
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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