Water → HCID 86721475, compound

HRID 869613Notes

Reaction equation

HRID 869613 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:8]([C:10]#[C:11][Si](C)(C)C)[CH:7]=[CH:6][N:5]2[C:16]=1[CH2:17][C:18]1[CH:37]=[CH:36][C:21]2/[C:22](=[C:32](/[CH3:35])\[C:33]#[N:34])/[C:23]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=3[O:25][CH2:26][C:20]=2[CH:19]=1.O>C1COCC1>[C:10]([C:8]1[CH:7]=[CH:6][N:5]2[C:16]([CH2:17][C:18]3[CH:37]=[CH:36][C:21]4/[C:22](=[C:32](/[CH3:35])\[C:33]#[N:34])/[C:23]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=5[O:25][CH2:26][C:20]=4[CH:19]=3)=[C:2]([CH3:1])[N:3]=[C:4]2[CH:9]=1)#[CH:11]

Participants

4

Reactant 2

HCID 962WaterHCID 86721476HCID 86721476, compound

Product 1

HCID 86721475HCID 86721475, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[step 2] (E)-2-{8-[(2-methyl-7-trimethylsilylethynylimidazo[1,2-a]pyridin-3-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (340 mg, 0.62 mmol) obtained in step 1 was dissolved in THF (3 ml), 1 mmol/L tetrabutylammonium fluoride THF solution (0.81 ml, 0.81 mmol) was added, and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (heptane/ethyl acetate=1/2 v/v) to give the title compound (152 mg, 53%).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (heptane/ethyl acetate=1/2 v/v)

Sources & evidence

ORD record
ord-56cb624c0f4d4239ab319015dd13b201
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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