Methyl iodide → HCID 57634216, compound

HRID 2109756Notes

Reaction equation

HRID 2109756 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5]2.[H-].[Na+].I[CH3:23]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([N:12]([CH3:23])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68994103HCID 68994103, compound

Product 1

HCID 57634216HCID 57634216, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 6-bromoisoquinolin-3-ylcarbamate (48 g, 1.5 mmol) was taken up in 10 mL of DMF and chilled to 0° C. Sodium hydride (0.074 g, 1.9 mmol) was added, and the mixture was stirred for 15 minutes. Iodomethane (0.10 mL, 1.6 mmol) was then added, and the mixture was stirred for 30 minutes. The reaction mixture was then quenched with 5 mL of aq NH4Cl. The mixture was then diluted with 50 mL of EtOAc and transferred to a separatory funnel. The mixture was washed five times with 25 mL of water and once with 25 mL of brine. The remaining portion was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (0.5% to 7.5% EtOAc/hexanes), affording tert-butyl 6-bromoisoquinolin-3-yl(methyl)carbamate (0.39 g, 78% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.04 (s, 1H) 7.95 (s, 1H) 7.88 (s, 1H) 7.77 (d, J=8.80 Hz, 1H) 7.56 (dd, J=8.61, 1.76 Hz, 1H) 3.48 (s, 3H) 1.57-1.52 (m, 9H).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe reaction mixture was then quenched with 5 mL of aq NH4Cl
  3. additionThe mixture was then diluted with 50 mL of EtOAc
  4. customtransferred to a separatory funnel
  5. washThe mixture was washed five times with 25 mL of water
  6. dry with materialThe remaining portion was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (0.5% to 7.5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b34706024b724fc7a71b087e0b414dd7
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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