tert-Butanol → HCID 59426033, compound

HRID 252547Notes

Reaction equation

HRID 252547 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH3:14])=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[NH:25][CH2:26][C:27]([O:29]CC)=O)=[CH:19][CH:18]=1)#[N:2].CC(C)([O-])C.[K+].C(O)(C)(C)C>C1COCC1>[O:32]=[C:24]1[NH:25][CH2:26][C:27](=[O:29])[N:23]1[C:20]1[CH:19]=[CH:18][C:17]([C:4]2[N:5]([CH2:15][CH3:16])[C:6]3[C:11]([C:3]=2[C:1]#[N:2])=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH3:14])[CH:7]=3)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 59424910HCID 59424910, compound2×

Product 1

HCID 59426033HCID 59426033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl {3-[4-(3-cyano-6-ethoxy-1-ethyl-1H-indol-2-yl)-phenyl]-ureido}-acetate (compound 773, 101 mg, 0.232 mmol) in THF (10 mL) is treated with a solution of potassium tert-butoxide in tert-butanol (0.30 mL, 1.0 M, 0.30 mmol), and the resulting mixture is allowed to stir overnight. The reaction mixture is partitioned between water and ethyl acetate (50 mL each), and the organic phase is washed with saturated brine. The aqueous phases are extracted with more ethyl acetate, and the extracts are combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual material is separated by column chromatography (eluting 2/1 ethyl acetate/hexane on silica gel 60) to afford 2-[4-(2,5-dioxo-imidazolidin-1-yl)-phenyl]-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile, compound 779, which is purified further by trituration with ether, collection by filtration and drying under high vacuum (76 mg, 0.196 mmol, 84%).

Workup

  1. customThe reaction mixture is partitioned between water and ethyl acetate (50 mL each)
  2. washthe organic phase is washed with saturated brine
  3. extractionThe aqueous phases are extracted with more ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual material is separated by column chromatography (eluting 2/1 ethyl acetate/hexane on silica gel 60)

Sources & evidence

ORD record
ord-a19e021161e0452f8aa1b84836815a69
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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