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

HRID 1270866Notes

Reaction equation

HRID 1270866 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-9da421e379834945ae67a45326b86eca
Source dataset
uspto-grants-2007_04
Patent number
US07202363B2

Reaction notes

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