tert-Butanol → HCID 59426033, compound

HRID 907155Notes

Reaction equation

HRID 907155 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) was treated with a solution of potassium tert-butoxide in tert-butanol (0.30 mL, 1.0 M, 0.30 mmol), and the resulting mixture was allowed to stir overnight. The reaction mixture was partitioned between water and ethyl acetate (50 mL each), and the organic phase was washed with saturated brine. The aqueous phases were extracted with more ethyl acetate, and the extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual material was 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 was 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 was partitioned between water and ethyl acetate (50 mL each)
  2. washthe organic phase was washed with saturated brine
  3. extractionThe aqueous phases were extracted with more ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual material was separated by column chromatography (eluting 2/1 ethyl acetate/hexane on silica gel 60)

Sources & evidence

ORD record
ord-611b47895b7747cc8f2d23214fe82639
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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