Methyl iodide → HCID 68784434, compound

HRID 80188Notes

Reaction equation

HRID 80188 reaction equation
[Br:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].CI.[CH2:17](OC(=O)C)C>CN(C=O)C.CCCCCC>[Br:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH3:17])[CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 533932493-Bromo-1H-indole-4-carbonitrile

Product 1

HCID 68784434HCID 68784434, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-1H-indole-4-carbonitrile (I-146a: 500 mg, 2.272 mmol) was added dropwise to a stirred mixture of NaH (0.218 g, 9.0833 mmol) in dry DMF (15 mL) at 0° C. over a period of 10 minutes. This was followed by the addition of methyl iodide and the resulting mixture was stirred at 0° C. for 2 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was quenched with ice water; the precipitate formed was collected and dried to afford 0.400 g of the crude product.

Workup

  1. customThe reaction mixture was quenched with ice water
  2. customthe precipitate formed
  3. customwas collected
  4. customdried

Sources & evidence

ORD record
ord-fe7571c1bd6646c4b46fa82476120ef4
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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