2-Methyl-3-butyn-2-ol → 4-(1H-indol-5-yl)-2-methyl-but-3-yn-2-ol

HRID 1443789Notes

Reaction equation

HRID 1443789 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:36][C:37]([OH:41])([C:39]#[CH:40])[CH3:38]>[Cu]I.[Pd].COCCOC>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([C:40]#[C:39][C:37]([CH3:38])([OH:41])[CH3:36])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

8

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27823135-Iodo-1H-indole

Product 1

HCID 668793284-(1H-indol-5-yl)-2-methyl-but-3-yn-2-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-iodoindole (25 g, 102.9 mmol), triphenylphosphine (2.70 g, 10.3 mmol), CuI (1.96 g, 10.3 mmol), potassium carbonate (35.5 g, 257.2 mmol), palladium (5 wt. % on calcium carbonate, poisoned with lead) (0.55 g, 5.14 mmol) and 1,2-dimethoxyethane (250 ml) was stirred at room temperature for 0.5 hour. 2-Methyl-3-butyn-2-ol (21.6 g, 257 mmol) was added and the mixture was stirred for 15 hours at 100° C. The crude mixture was filtered through silica gel and aqueous hydrochloric acid (250 ml, 2 M) was added and extracted with toluene. The organic phase was dried and evaporated. Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound. Yield 6.7 g (33%). Mp. 119-123° C.

Workup

  1. stirringthe mixture was stirred for 15 hours at 100° C
  2. filtrationThe crude mixture was filtered through silica gel and aqueous hydrochloric acid (250 ml, 2 M)
  3. additionwas added
  4. extractionextracted with toluene
  5. customThe organic phase was dried
  6. customevaporated

Sources & evidence

ORD record
ord-f29690ea37364b2d9a3452c77918c547
Source dataset
uspto-grants-2010_02
Patent number
US07662812B2

Reaction notes

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