Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-3-thienyl)-5-[5-(1-pyrrolidinylmethyl)-3-thienyl]-1H-indole-7-carboxamide

HRID 387361Notes

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.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]([CH2:34][N:35]3[CH2:41][CH2:40][CH2:39][CH2:38]CC3)[S:32][CH:33]=2)O1.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]>[O:19]=[S:16]1(=[O:20])[CH2:17][CH2:18][CH:14]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:29]4[CH:30]=[C:31]([CH2:34][N:35]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[S:32][CH:33]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide (0.035 g, 0.098 mmol) and 1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}hexahydro-1H-azepine (0.038 g, 0.130 mmol, 1.3 eq) was dissolved in a 6:1 solution of 1,4 dioxane/water in a 20 mL microwave reaction vessel. Potassium carbonate (0.068, 0.490 mmol, 5 eq) was added and the solution was degassed with Argon. PdCl2(dppf) (0.012 g, 0.017 mmol, 0.17 eq) 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 0.0052 g (12%) 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-ebd886922ea749549fa159c943e0612f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372875B2

Reaction notes

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