Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(1,3-thiazol-2-yl)-1H-indole-7-carboxamide

HRID 387340Notes

Reaction equation

HRID 387340 reaction equation
[O:1]=[S:2]1(=[O:29])[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[C:12]([C:26]([NH2:28])=[O:27])[CH:13]=[C:14](B4OC(C)(C)C(C)(C)O4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[C:31]1[S:32][CH:33]=[CH:34][N:35]=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].C(Cl)Cl>[O:1]=[S:2]1(=[O:29])[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[C:12]([C:26]([NH2:28])=[O:27])[CH:13]=[C:14]([C:31]4[S:32][CH:33]=[CH:34][N:35]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 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 593327273-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(1,3-thiazol-2-yl)-1H-indole-7-carboxamideYield 25%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (60 mg, 0.14 mmol), 2-bromo-1,3-thiazole (29 mg, 1.2 eq), PdCl2(dppf)-CH2Cl2 adduct (19 mg, 0.02 mmol, 0.16 eq), potassium carbonate (90 mg, 4.6 eq) were diluted in a mixture of dioxane (3 mL) and water (1.5 mL) in a 2-5 mL biotage microwave reaction tube. After the mixture was degassed by bubbling argon through for 5 minutes, it was heated in a biotage microwave at normal absorption for 5 minutes at 10° C. The reaction mixture was filtered through a thiol SPE cartridge (polymer labs), then was concentrated and purified by ammonium hydroxide gilson hplc. The desired fractions were combined and concentrated in an EZ2 Genevac evaporator, giving the title compound (12 mg, 25%).

Workup

  1. customAfter the mixture was degassed
  2. customby bubbling argon through for 5 minutes, it
  3. filtrationThe reaction mixture was filtered through a thiol SPE cartridge (polymer labs)
  4. concentrationwas concentrated
  5. custompurified by ammonium hydroxide gilson hplc
  6. concentrationconcentrated in an EZ2 Genevac evaporator

Sources & evidence

ORD record
ord-1ca183dcfe7e4b599161914e54d5737e
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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