Potassium Carbonate → (Rac)-3-(1,1-dioxidotetrahydro-3-thienyl)-5-(4-fluorophenyl)-1h-indole-7-carboxamide

HRID 656118Notes

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.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.O1CCOCC1>[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:25]4[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15]1

Participants

Conditions

Temperature: 150 °C

Procedure

5-Bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide (100 mg, 0.28 mmol), and dioxane water (3:1, 2 mL) were dissolved together. 4-fluorophenyl boronic acid (59 mg, 0.42 mmol), potassium carbonate (116 mg, 0.84 mmol) were added and a stream of Ar was passed through the solution for 5 min and then Pd(PPh3)4 was added (32 mg, 0.028 mmol). Argon was passed through the solution for 5 min and then the mixture was heated on the microwave at 150° C. for 20 min. The reaction mixture was concentrated and purified by HPLC to afforded 17 mg of the title compound.

Workup

waitArgon was passed through the solution for 5 min
concentrationThe reaction mixture was concentrated
custompurified by HPLC

Sources & evidence

ORD record: ord-2328b2ebb85d499eaabf502659198a1b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071584B2

Reaction notes

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