Ethyl Acetate → HCID 67210582, compound

HRID 452139Notes

Reaction equation

HRID 452139 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].Cl[CH2:13][C:14]1[CH:32]=[CH:31][C:17]2/[C:18](=[C:27](/[CH3:30])\[C:28]#[N:29])/[C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[O:21][CH2:22][C:16]=2[CH:15]=1.C(OCC)(=O)C>CN(C=O)C>[N:1]1([CH2:13][C:14]2[CH:32]=[CH:31][C:17]3/[C:18](=[C:27](/[CH3:30])\[C:28]#[N:29])/[C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[O:21][CH2:22][C:16]=3[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[N:1]1[N:2]([CH2:13][C:14]2[CH:32]=[CH:31][C:17]3/[C:18](=[C:27](/[CH3:30])\[C:28]#[N:29])/[C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[O:21][CH2:22][C:16]=3[CH:15]=2)[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 92211H-IndazoleHCID 24758Sodium hydrideHCID 67211222HCID 67211222, compound

Product 2

HCID 67210409HCID 67210409, compoundYield 36%HCID 67210582HCID 67210582, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[step 1] Indazole (240 mg, 2.03 mmol) was dissolved in DMF (5.0 mL), sodium hydride (60%, 81 mg, 2.03 mmol) was added, and the mixture was stirred for 15 min. To this mixture was added (E)-2-(8-chloromethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrile (300 mg, 1.01 mmol) obtained in Reference Example B5, and the mixture was stirred at room temperature for 3 hr. Ethyl acetate was added to the mixture, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to give (E)-2-[8-(indazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (245 mg, 64%) and (E)-2-[8-(indazol-2-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (138 mg, 36%).

Workup

  1. customobtained in Reference Example B5
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)

Sources & evidence

ORD record
ord-7a11613c817045778409554aed224dd7
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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