Dimethyl Sulfoxide → HCID 67202863, compound

HRID 1624981Notes

Reaction equation

HRID 1624981 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:29].C([O-])([O-])=O.[Na+].[Na+]>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[I:29])[C:7]2=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 23668193Sodium NitriteHCID 58270444HCID 58270444, compound

Product 1

HCID 67202863HCID 67202863, compound

Conditions

Temperature
35 °C

Procedure

5-Amino-2-(4-fluorobenzyl)isoquinolin-1(2H)-one (0.6 g, 0.002 mol) was added to a solution of sodium nitrite (0.5 g, 0.008 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) at 35° C. Aqueous hydrogen iodide (2 mL, 0.02 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) was added. The reaction mixture was stirred at 35° C. for 1 hour. The cooled reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×20 mL). The combined methylene chloride extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed on 12 g of silica gel column (0-50% EtOAc/Hexane) gave the desired product as a brown solid. MS m/z (M+H) 379.7.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with methylene chloride (3×20 mL)
  3. washThe combined methylene chloride extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on 12 g of silica gel column (0-50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-4f0832ac55a04797824da14dd7b305f7
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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