Tetrahydrofuran → HCID 59802494, compound

HRID 1672141Notes

Reaction equation

HRID 1672141 reaction equation
[Cl:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1.C1COCC1.[H][H]>[OH-].[OH-].[Pd+2].CO>[Cl:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 59802492HCID 59802492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59802494HCID 59802494, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

32.6 grams (0.118 mol) of 7-chloro-3-cyclohexenyl-1H-indole-6-carboxylic acid was added to a one liter round bottom flask along with 250 mL of a 1:1 (v/v) mixture of THF and methanol. 3.3 grams of 20% palladium hydroxide on carbon was then added and the flask was fitted with a septa and balloon of hydrogen. The mixture was stirred overnight at room temperature. In the morning, the crude product was filtered through a pad of celite and the pad was washed with THF. The product was evaporated to dryness and triturated with cold diethyl ether to give 32.1 grams of a tan solid (98% yield, 85% purity, UV detection λ=220 nm) that was used without further purification. MS m/z 278.00 (M+H).

Workup

  1. filtrationIn the morning, the crude product was filtered through a pad of celite
  2. washthe pad was washed with THF
  3. customThe product was evaporated to dryness
  4. customtriturated with cold diethyl ether

Sources & evidence

ORD record
ord-53a11a2d0a5443dca90bd44b8eb184b2
Source dataset
uspto-grants-2011_08
Patent number
US07998951B2

Reaction notes

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