Tetrahydrofuran → HCID 86646303, compound

HRID 1027133Notes

Reaction equation

BrC1C=NN2C(NCC3C=CC=C(F)C=3)=C([C:20]([N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[O:21])C=NC=12.CC1C[C:37]2[C:42]([CH:43]=1)=[CH:41]C=CC=2.[H-].[Na+].C(=O)([O-])[OH:47].[Na+].[CH2:51]1[CH2:55]OC[CH2:52]1>>[CH3:55][C:51]1[C:25]2([CH2:24][CH2:23][N:22]([C:20]([O:21][C:42]([CH3:41])([CH3:37])[CH3:43])=[O:47])[CH2:27][CH2:26]2)[C:28]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:52]=1

Participants

Reactant 5

HCID 8028Tetrahydrofuran

HCID 165871H-Indene, 2-methyl-

HCID 24758Sodium hydride

HCID 516892Sodium Bicarbonate

HCID 67540544HCID 67540544, compound

Product 1

HCID 86646303HCID 86646303, compoundYield 51%

Procedure

tert-Butyl bis(2-chloroethyl)carbamate (1.33 g, 5.49 mmol) obtained in step 1 was dissolved in THF, 2-methylinden (1.00 g, 7.69 mmol) and sodium hydride (2.16 g, 49.4 mmol) were added under ice-cooling, and the mixture was heated under reflux for 3 hr. The reaction mixture was added dropwise to saturated aqueous sodium hydrogen carbonate solution under ice-cooling, and the mixture was extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give the title compound (1.19 g, 51%).

Workup

temperaturecooling
temperaturethe mixture was heated
temperatureunder reflux for 3 hr
temperaturecooling
extractionthe mixture was extracted several times with ethyl acetate
dry with materialThe combined organic layers were dried over magnesium sulfate
customevaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-2f4323386b754ca5bcda6bc9741f2e5c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729264B2

Reaction notes

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