Potassium Carbonate → HCID 59332784, compound

HRID 387338Notes

Reaction equation

HRID 387338 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.[O:8]=[S:9]1(=[O:36])[CH2:14][CH2:13][CH:12]([C:15]2[C:23]3[C:18](=[C:19]([C:33]([NH2:35])=[O:34])[CH:20]=[C:21](B4OC(C)(C)C(C)(C)O4)[CH:22]=3)[NH:17][CH:16]=2)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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>[Br:7][C:5]1[N:6]=[C:2]([C:21]2[CH:22]=[C:23]3[C:18](=[C:19]([C:33]([NH2:35])=[O:34])[CH:20]=2)[NH:17][CH:16]=[C:15]3[CH:12]2[CH2:11][CH2:10][S:9](=[O:8])(=[O:36])[CH2:14][CH2:13]2)[S:3][CH:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27632972,4-Dibromo-1,3-thiazoleHCID 593327113-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide

Product 1

HCID 59332784HCID 59332784, compoundYield 4.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a microwave vial was added 2,4-dibromo-1,3-thiazole (0.035 g, 0.143 mmol), 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (0.060 g, 0.143 mmol) and potassium carbonate (0.059 g, 0.429 mmol) along with 1,4-dioxane (1.073 mL)/water (0.358 mL). The mixture was degassed with nitrogen and Pd(PPh3)4 (0.017 g, 0.014 mmol) was added. The reaction mixture was heated in the microwave under ‘high’ absorption setting for 40 minutes at 150° C. The reaction mixture was filtered through a Thiol SPE cartridge (500 mg) eluting with 1:1 MeOH/DCM (10 mL). The eluent was concentrated under nitrogen and purified by RP-HPLC on an X-Bridge C18 column with Acetonitrile/Water (0.1% NH4OH), giving 3 mg (4.6%) of the title compound.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated in the microwave under ‘high’
  3. customabsorption
  4. filtrationThe reaction mixture was filtered through a Thiol SPE cartridge (500 mg)
  5. washeluting with 1:1 MeOH/DCM (10 mL)
  6. concentrationThe eluent was concentrated under nitrogen
  7. custompurified by RP-HPLC on an X-Bridge C18 column with Acetonitrile/Water (0.1% NH4OH)

Sources & evidence

ORD record
ord-c69c91d9d4564096bceacf0128dd8abc
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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