Diisopropylamine → 1-ethyl-6-methoxy-2-tributylstannanyl-1H-indole-3-carbonitrile

HRID 505999Notes

Reaction equation

HRID 505999 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Li+].CC([N-]C(C)C)C.[CH2:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[C:25]([C:34]#[N:35])=[CH:24]1)[CH3:22].[CH2:36]([Sn:40](I)([CH2:45][CH2:46][CH2:47][CH3:48])[CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH3:39]>C1COCC1>[CH2:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[C:25]([C:34]#[N:35])=[C:24]1[Sn:40]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:45][CH2:46][CH2:47][CH3:48])[CH2:36][CH2:37][CH2:38][CH3:39])[CH3:22]

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 23765Tributyltin iodideHCID 2724682Lithium diisopropylamide2×HCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 594249491-ethyl-6-methoxy-2-tributylstannanyl-1H-indole-3-carbonitrileYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of THF (60 mL) and diisopropylamine (5.5 mL, 39 mmol) is cooled to −78° C. n-Butyllithium (14.5 mL, 2.5M in hexanes, 36.2 mmol) is added dropwise over 5 minutes. The LDA mixture is stirred at −78° C. for 10 minutes, and then at 0° C. for 20 minutes. The solution is re-cooled to −78° C. 1-ethyl-6-methoxy-1H-indole-3-carbonitrile (5.0 g, 25 mmol), prepared as in example 1A, is taken up in THF (30 mL) and added dropwise to the LDA mixture over 15 minutes. The reaction is stirred at −78° C. for 10 minutes, and at 0° C. for 30 minutes. Once again, the reaction mixture is cooled to −78° C. Tributyltin iodide (10 mL, 35 mmol) is added dropwise. This is stirred at −78° C. for 15 minutes, and then at 0° C. for 30 minutes. The reaction mixture is absorbed onto silica gel and concentrated. Purification by chromatography (CH2Cl2) yields 1-ethyl-6-methoxy-2-tributylstannanyl-1H-indole-3-carbonitrile (12.05 g, 98%).

Workup

  1. additionis added dropwise over 5 minutes
  2. waitat 0° C. for 30 minutes
  3. temperatureOnce again, the reaction mixture is cooled to −78° C
  4. stirringThis is stirred at −78° C. for 15 minutes
  5. waitat 0° C. for 30 minutes
  6. customThe reaction mixture is absorbed onto silica gel
  7. concentrationconcentrated
  8. customPurification by chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-1344400d031642d09108330baffa20f2
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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