Water → 7-Iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine

HRID 510170Notes

Reaction equation

HRID 510170 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[N:9]=2)[NH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1.O>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[CH:15][CH:16]=3)[N:9]=2)[N:4]([S:38]([C:35]2[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=2)(=[O:40])=[O:39])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66764117HCID 66764117, compound

Product 1

HCID 667631397-Iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazineYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-iodo-2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine (5.0 g, 11.70 mmol) and DIPEA (3.024 g, 4.075 mL, 23.40 mmol) in DMF (25.00 mL) was added p-toluenesulfonyl chloride (2.454 g, 12.87 mmol). The resulting solution was stirred at room temperature for 2 hours. Water was added and the resultant precipitate collected, dried in vacuo at 40° C. to give the sub-title compound as an off-white solid (6.61 g, 97.16%). 1H NMR (400.0 MHz, DMSO) δ 9.18 (s, 1H), 8.64 (s, 1H), 8.42 (d, 2H), 8.05 (q, 4H), 7.48 (d, 2H), 3.50-3.45 (m, 1H), 2.36 (s, 3H) and 1.22-1.19 (m, 6H) ppm; MS (ES+) 581.9.

Workup

  1. customthe resultant precipitate collected
  2. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-bc47bc169b244421b6bf6e5cae5ba6dd
Source dataset
uspto-grants-2015_08
Patent number
US09096602B2

Reaction notes

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