Dichloromethane → 2-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

HRID 390108Notes

Reaction equation

HRID 390108 reaction equation
[I:1]Cl.ClCCl.[Cl:6][C:7]1[N:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1>N1C=CC=CC=1>[Cl:6][C:7]1[N:8]=[C:9]2[C:15]([I:1])=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24640Iodine chlorideHCID 457896382-Chloro-5H-pyrrolo[2,3-B]pyrazine

Product 1

HCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazineYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A 1 M solution of iodine monochloride in dichloromethane (9.84 mL, 9.84 mmol) was added dropwise to an ice-cold solution of 2-chloro-5H-pyrrolo[2,3-b]pyrazine (6.75 g, 11.07 mmol) in anhydrous pyridine (12 mL). The reaction mixture was stirred at 0° C. for 60 minutes, then concentrated. The residue was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The crude product was stirred with 15 mL of dichloromethane. The yellow solid material was collected by filtration, washed with dichloromethane and dried to give 2.86 g of the title product. Yield: 66%. MS (DCI+) m/z 280 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated
  5. stirringThe crude product was stirred with 15 mL of dichloromethane
  6. filtrationThe yellow solid material was collected by filtration
  7. washwashed with dichloromethane
  8. customdried

Sources & evidence

ORD record
ord-62318aa24301476089a5ce1db8fab759
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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