[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine → 1-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole

HRID 491032Notes

Reaction equation

HRID 491032 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]#[C:23][CH:24]2[CH2:26][CH2:25]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CN(C)C=O.[Cu]I>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([N:15]2[C:16]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:22]=[C:23]2[CH:24]2[CH2:25][CH2:26]2)[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57675733[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine

Product 1

HCID 576757611-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of [4-(tert-butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine (3.84 g, 10.4mmol) in N,N-dimethylformamide (60 mL) was added copper(I) iodide (100 mg, 0.525 mmol). After the reaction was refluxed for 48 hours, it was allowed to cool to room temperature, and the solvent was removed in vacuo. The residue was partitioned between water and dichloromethane. The dichloromethane was dried (MgSO4) and concentrated to give a dark residue that was used in the next step with no further purification. LC-MS (C23H35NOSi calc'd 369) m/z 370 (M+H).

Workup

  1. temperatureAfter the reaction was refluxed for 48 hours
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between water and dichloromethane
  4. dry with materialThe dichloromethane was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give a dark residue that
  7. customwas used in the next step with no further purification

Sources & evidence

ORD record
ord-ac016e5a18a644f5a0643dcb74e8b433
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Reaction notes

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