Dichloromethane → HCID 66764117, compound

HRID 510169Notes

Reaction equation

HRID 510169 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH:21]=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[I:22]Cl.ClCCl.CCOC(C)=O>N1C=CC=CC=1>[I:22][C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:10]3[CH:9]=[CH:8][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[CH:12][CH:11]=3)[N:14]=2)[NH:19][CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 24640Iodine chlorideHCID 667640832-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 66764117HCID 66764117, compoundYield 46.79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine (9 g, 29.86 mmol) in pyridine (90.00 mL) at RT was added a 1M solution of iodine monochloride in dichloromethane (32.85 mL of 1 M, 32.85 mmol). The resulting dark brown solution was stirred at RT for 4 hours then taken into EtOAc and washed with aqueous sodium thiosulphate/NaHCO3×2 then with brine, then dried over MgSO4 and concentrated under reduced pressure. The solid residue was triturated with acetonitrile, filtered and washed with acetonitrile, dried in vacuo to give the subtitle compound (5.97 g, 13.97 mmol, 46.79%). 1H NMR (400.0 MHz, DMSO) δ 12.72 (s, 1H), 9.03 (s, 1H), 8.46 (d, J=8.5 Hz, 2H), 8.23 (s, 1H), 8.01 (d, J=8.5 Hz, 2H), 3.49 (t, J=6.8 Hz, 1H) and 1.20 (d, J=6.8 Hz, 6H) ppm; MS (ES+) 428.0.

Workup

  1. washwashed with aqueous sodium thiosulphate/NaHCO3×2
  2. dry with materialwith brine, then dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe solid residue was triturated with acetonitrile
  5. filtrationfiltered
  6. washwashed with acetonitrile
  7. customdried in vacuo

Sources & evidence

ORD record
ord-52fbf83a33ea45c1a2ef98f073b09f33
Source dataset
uspto-grants-2015_08
Patent number
US09096602B2

Reaction notes

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