Water → HCID 59332669, compound

HRID 387331Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)=[O:2].Br[C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([C:22]([NH2:24])=[O:23])[CH:21]=1)[NH:18][CH:17]=[C:16]2[CH:25]1[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:32]=[S:28]1(=[O:31])[CH2:29][CH2:30][CH:25]([C:16]2[C:15]3[C:19](=[C:20]([C:22]([NH2:24])=[O:23])[CH:21]=[C:13]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([CH:1]=[O:2])[CH:4]=4)[CH:14]=3)[NH:18][CH:17]=2)[CH2:26][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (3-formylphenyl)boronic acid (0.121 g, 0.808 mmol), 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (0.150 g, 0.404 mmol) and Potassium carbonate (0.168 g, 1.212 mmol) in 1,4-Dioxane (1.796 mL)/Water (0.898 mL) was degassed with nitrogen for several minutes and PdCl2(dppf) (0.030 g, 0.040 mmol) was added. The mixture was heated at 100° C. for 5 minutes in the microwave on ‘high’ absorption setting. The aqueous layer was removed via pipette and the reaction mixture was filtered through a 500 mg Stratospheres PL Thiol SPE cartridge, eluting with 10 mL of DCM/MeOH (1:1). Crude LCMS shows the desired compound as major peak. Concentrated under nitrogen to obtain 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-formylphenyl)-1H-indole-7-carboxamide (0.160 g, 0.404 mmol, 100% yield).

Workup

customwas degassed with nitrogen for several minutes
customabsorption setting
customThe aqueous layer was removed via pipette
filtrationthe reaction mixture was filtered through a 500 mg Stratospheres PL Thiol SPE cartridge
washeluting with 10 mL of DCM/MeOH (1:1)
concentrationConcentrated under nitrogen

Sources & evidence

ORD record: ord-1ed987787e80490b98ca1fd48d7c745e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372875B2

Reaction notes

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