Iodine chloride → 2-iodo-4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1727837Notes

Reaction equation

[I:1]Cl.[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[C:16]([Si](C)(C)C)=[CH:17][C:10]=23)[C:6]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[N:5]1>C(#N)C>[I:1][C:16]1[N:15]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:11]2=[N:12][CH:13]=[CH:14][C:9]([C:7]3[C:6]([C:31]4[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=4)=[N:5][N:4]([CH3:3])[CH:8]=3)=[C:10]2[CH:17]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of ICl (1M in CH2Cl2, 43.3 mmol) in acetonitrile (250 ml) at −10° C. was added a solution of 4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine (8.67 mmol) in acetonitrile (46 ml) followed by stirring at −10° C. for 5 minutes. The reaction was concentrated to approx. ⅓ total volume and then diluted with EtOAc (500 ml). The solution was washed with saturated NaHCO3(aq) (100 ml), saturated Na2S2O3(aq) (100 ml), brine (100 ml), and dried over MgSO4. Filtration and concentration in vacuo yielded a tan solid which was triturated with hot acetonitrile/Et2O, providing the title product as a light tan solid (53%). ESMS [M+H]+: 586.0.

Workup

concentrationThe reaction was concentrated to approx. ⅓ total volume
additiondiluted with EtOAc (500 ml)
washThe solution was washed with saturated NaHCO3(aq) (100 ml), saturated Na2S2O3(aq) (100 ml), brine (100 ml)
dry with materialdried over MgSO4
filtrationFiltration and concentration in vacuo
customyielded a tan solid which
customwas triturated with hot acetonitrile/Et2O

Sources & evidence

ORD record: ord-357de95834b249348c53a10f7f7bc659
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495102B2

Reaction notes

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