Potassium Carbonate → HCID 25072228, compound

HRID 387365Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]1.[S:21]1[C:25]2[CH:26]=[CH:27][C:28](B(O)O)=[CH:29][C:24]=2[CH:23]=[CH:22]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[S:21]1[C:25]2[CH:26]=[CH:27][C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=3)[NH:7][CH:6]=[C:5]4[CH:14]3[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]3)=[CH:29][C:24]=2[CH:23]=[CH:22]1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide (0.06 g, 0.168 mmol) and 1-benzothien-5-ylboronic acid (0.036 g, 0.202 mmol) was dissolved in a 6:1 solution of 1,4 dioxane/water in a 20 mL microwave reaction vessel. Potassium carbonate (0.113 g, 0.816 mmol) was added and the solution was degassed with Argon. PdCl2(dppf) (0.025 g, 0.034 mmol) was added and the reaction was heated in a microwave at 100° C. for 20 min. The solution was passed through a StratoSphere SPE PL-Thiol MP SPE column to remove palladium and purified on Gilson preparative HPLC using Acetonitrile/Water with 0.1% TFA. The desired fractions were concentrated, giving 0.044 g (67%) of the title compound.

Workup

customthe solution was degassed with Argon
customto remove palladium
custompurified on Gilson preparative HPLC
concentrationThe desired fractions were concentrated

Sources & evidence

ORD record: ord-52a1e972d9fe493ea79be21e90629349
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372875B2

Reaction notes

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