Methanol → (2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]-2-propen-1-ol

HRID 17142Notes

Reaction equation

HRID 17142 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:24]=[CH:25]/[C:26](OCC)=[O:27])=[CH:4][N:3]=1.CC(C[AlH]CC(C)C)C.CO>C1COCC1>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:24]=[CH:25]/[CH2:26][OH:27])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 69775446Ethyl (2e)-3-[4-amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylate

Product 1

HCID 18450606(2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]-2-propen-1-olYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 223 (0.45 g, 10.8 mmol) in THF at −78° C. was treated with 5.4 mL DIBAL-H solution (1.0M in toluene, 5.4 mmol) and methanol (1 mL), warmed to room temperature, and concentrated. The residue was dissolved in methanol (100 mL), treated with silica gel (5 g), and concentrated. The preabsorbed silica gel was subsequently transferred to a silica gel column and chromatographed (ethyl acetate/heptane 3:1) to provide 200 mg (49%) of the product.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol (100 mL)
  3. additiontreated with silica gel (5 g)
  4. concentrationconcentrated
  5. customchromatographed (ethyl acetate/heptane 3:1)

Sources & evidence

ORD record
ord-8f6bea5b969e4a678b06891b9e1d373f
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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