Tetrahydrofuran → HCID 90197436, compound

HRID 869583Notes

Reaction equation

HRID 869583 reaction equation
[C:1](/[C:3](=[C:5]1/[C:6]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH2:16][C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25](C(OCCC)=O)[C:20]4=N[C:18]=3[CH:32]3[CH2:34][CH2:33]3)[CH:13]=[CH:12][C:11]/1=2)/[CH3:4])#[N:2].[CH3:40][Mg]Cl.[Cl-].[NH4+:44].[CH2:45]1[CH2:49][O:48]CC1>>[CH:32]1([C:18]2[N:44]=[C:20]3[C:25]([C:49]([OH:48])([CH3:45])[CH3:40])=[CH:24][CH:23]=[CH:22][N:21]3[C:17]=2[CH2:16][C:14]2[CH:13]=[CH:12][C:11]3/[C:5](=[C:3](/[CH3:4])\[C:1]#[N:2])/[C:6]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:7]=4[O:8][CH2:9][C:10]=3[CH:15]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 131732527HCID 131732527, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 90197436HCID 90197436, compoundYield 90%

Conditions

Temperature
-20 °C

Procedure

[step 2] (E)-propyl 3-{[11-(1-cyanoethylidene)-3-fluoro-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl}-2-cyclopropylimidazo[1,2-a]pyridine-8-carboxylate (350 mg, 0.55 mmol) obtained in step 1 was dissolved in THF (4.1 mL), methylmagnesium chloride (3 mol/L THF solution, 0.73 mL, 2.20 mmol) was added at −30° C., and the mixture was stirred at −20° C. for 2 hr. To the mixture was added saturated aqueous ammonium chloride solution, 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 residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-70/30 v/v) to give the title compound (244 mg, 90%).

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 residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-70/30 v/v)

Sources & evidence

ORD record
ord-137666b2904f46cd808fbdd6cf11699f
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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