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

HRID 17160Notes

Reaction equation

HRID 17160 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-e9722cb53f9e4f5980965732bf189dbb
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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