Iodine → HCID 24863927, compound

HRID 910647Notes

Reaction equation

HRID 910647 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[N:14]=2)[CH:11]=1)CCC.[I:30]I.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[N:14]=[C:9]3[CH:8]=[N:7][C:6]([I:30])=[CH:11][N:10]3[CH:12]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 24863928HCID 24863928, compound

Product 1

HCID 24863927HCID 24863927, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

314 mg (corresponding to 0.628 mmol) of 6-tributylstannyl-2-[4′-hydroxyphenyl]imidazo[1,2-a]pyrazine obtained from Example II-2 was dissolved in 5.0 mL of dichloromethane, to which 114 mg (corresponding to 0.942 mmol) of iodine dissolved in 5.0 mL of dichloromethane was added. The reaction mixture was stirred at the temperature of 0° C. for 10 minutes and at room temperature for 30 hours. Then, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium thiosulfate solution were added thereto. Precipitates were filtered and recovered, washed with water and ethyl acetate in this order, and dried under reduced pressure, to obtain 131 mg (corresponding to 0.389 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyrazine (FIG. 12, Step 1).

Workup

  1. additionwas added
  2. customPrecipitates
  3. filtrationwere filtered
  4. customrecovered
  5. washwashed with water and ethyl acetate in this order
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9ce98098e8264646b880b5cdf7464607
Source dataset
uspto-grants-2011_09
Patent number
US08022207B2

Reaction notes

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