Sodium Carbonate → 3-(2-tert-butoxy-6-chloropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 68338Notes

Reaction equation

[C:1]([O:5][C:6]1[CH:11]=[C:10](I)[CH:9]=[C:8]([Cl:13])[N:7]=1)([CH3:4])([CH3:3])[CH3:2].C(COC)OC.C(O)C.[C:23]1([S:29]([N:32]2[C:36]3=[N:37][CH:38]=[CH:39][CH:40]=[C:35]3[C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33]2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]1[CH:11]=[C:10]([C:34]2[C:35]3[C:36](=[N:37][CH:38]=[CH:39][CH:40]=3)[N:32]([S:29]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)(=[O:31])=[O:30])[CH:33]=2)[CH:9]=[C:8]([Cl:13])[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of EXAMPLE 34A (2.6 g, 8.35 mmol) in 5:1 dimethoxyethane/ethanol (90 mL) was added 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (3.53 g, 9.18 mmol), 1M aqueous sodium carbonate (6.68 mL) and dichlorobis (triphenylphosphine)-palladium (II) (0.29 g, 0.42 mmol). The reaction was heated at 80° C. for 3 hours, cooled, and diluted with ethyl acetate. The solution was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound. MS (ESI) m/e 442.0 (M+H)+.

Workup

temperaturecooled
washThe solution was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a6c5fcabb7274ee89202bbec57ee8a3f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822446B2

Reaction notes

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