4-Toluenesulfonyl chloride → 5-(2,6-difluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine

HRID 1529334Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:14]=[C:13]2[C:15]([I:18])=[CH:16][NH:17][C:12]2=[CH:11][CH:10]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:14]=[C:13]2[C:15]([I:18])=[CH:16][N:17]([S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[C:12]2=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 5-(2,6-difluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine (657 mg, 1.845 mmol) in THF (18 mL) was treated with 4-toluenesulfonyl chloride (387 mg, 2.029 mmol, Aldrich) and solid NaOH (89 mg, 2.214 mmol, VWR). The reaction was stirred at 23° C. under N2. After 45 min, the solution was diluted with EtOAc (200 ml) and washed with brine (150 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 10-30% EtOAc/hexane), affording 5-(2,6-difluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine.

Workup

washwashed with brine (150 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluent: 10-30% EtOAc/hexane)

Sources & evidence

ORD record: ord-a230afb50be44a7aadc9b060a8b6dc62
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090593B2

Reaction notes

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