Isopropanol → HCID 68996687, compound

HRID 1821385Notes

Reaction equation

HRID 1821385 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[O:20])=[N:2]1.C([Li])CCC.C[CH:32]([OH:34])C.[Cl-].[NH4+].C1C[O:40]CC1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([C:21]2[S:22][CH:23]=[CH:24][C:25]=2[C:32]([OH:34])=[O:40])=[O:20])=[N:2]1

Participants

6

Reactant 5

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 68999437HCID 68999437, compoundHCID 178418339Butyllithium

Product 1

HCID 68996687HCID 68996687, compoundYield 44%

Procedure

To a solution of (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}thiophene-2-carboxamide (0.28 g, 0.81 mmol) obtained in Example 14 in THF (5.6 mL), n-butyllithium (2.7 mol/L n-hexane solution, 3.0 mL, 8.1 mmol) was added dropwise at −78° C. under nitrogen atomosphere, followed by stirring for 1.0 hour. Then, under carbon dioxide gas atmosphere, the mixture was stirred at −78° C. for 30 minutes and at 0° C. for 2.0 hours. The reaction mixture was added with 2-propanol and saturated aqueous ammonium chloride solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 80/20) to obtain (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenylcarbamoyl}thiophene-3-carboxylic acid (0.14 g, 44%).

Workup

  1. stirringThen, under carbon dioxide gas atmosphere, the mixture was stirred at −78° C. for 30 minutes and at 0° C. for 2.0 hours
  2. extractionextracted with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 80/20)

Sources & evidence

ORD record
ord-6273ccb2ab22498e916e22eee1487314
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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