Methyl iodide → HCID 21833733, compound

HRID 1741057Notes

Reaction equation

HRID 1741057 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:14][CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:10]([I:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CI.[BH4-].[Na+].[C:26](=O)(O)[O-].[Na+]>CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:14][CH2:15][C:16]3[CH2:17][CH2:18][N:19]([CH3:26])[CH2:20][CH:21]=3)=[C:10]([I:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 21833804HCID 21833804, compound

Product 1

HCID 21833733HCID 21833733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Acetyl-2,3-dihydro-6-iodo-5-(pyridin-4-ylmethylthio)-1H-indole (D50) (0.390 g, 0.951 mmol) was dissolved in dry DMF (5 ml) and was treated with methyl iodide (0.089 ml, 1.430 mmol) with stirring. After 24 hours the reaction mixture was evaporated under reduced pressure and was triturated with ethyl acetate (~20 ml). The resultant brown solid was then filtered off, washed with diethyl ether and dried in vacuo (0.513 g). The solid was then redissolved in a mixture of ethanol (20 ml) and water (10 ml) and was cooled to 0° C. Sodium borohydride (0.069 g, 1.824 mmol) was then added. After 0.5 h a further amount of sodium borohydride (0.035 g, 0.912 mmol) was added. The reaction mixture was then allowed to warm to room temperature. After 1.5 hours the reaction mixture was treated with sodium bicarbonate solution (~15 ml) and was partitioned between dichloromethane and water. The aqueous layer was then extracted with dichloromethane (1X) and the combined organic layers were dried (Na2SO4) and evaporated under reduced pressure to give a yellow solid which was purified by silica-gel chromatography (5% MeOH/CH2Cl2 as eluant) to give the title compound as an off white solid (0.208 g, 53%).

Workup

  1. customAfter 24 hours the reaction mixture was evaporated under reduced pressure
  2. customwas triturated with ethyl acetate (~20 ml)
  3. filtrationThe resultant brown solid was then filtered off
  4. washwashed with diethyl ether
  5. customdried in vacuo (0.513 g)
  6. dissolutionThe solid was then redissolved in a mixture of ethanol (20 ml) and water (10 ml)
  7. temperatureto warm to room temperature
  8. customwas partitioned between dichloromethane and water
  9. extractionThe aqueous layer was then extracted with dichloromethane (1X)
  10. dry with materialthe combined organic layers were dried (Na2SO4)
  11. customevaporated under reduced pressure
  12. customto give a yellow solid which
  13. customwas purified by silica-gel chromatography (5% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-1ce8be33688444ddb77f00ad9e3d8f65
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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