Potassium Carbonate → HCID 66747490, compound

HRID 387391Notes

Reaction equation

HRID 387391 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[C@@H:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[C@@H:16]([CH:22]([CH3:24])[CH3:23])[CH2:15]1.[O:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]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]>[O:25]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=2)[NH:7][CH:6]=[C:5]3[C@@H:14]2[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[C@@H:16]([CH:22]([CH3:23])[CH3:24])[CH2:15]2)=[CH:26]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 66746207HCID 66746207, compound

Product 1

HCID 66747490HCID 66747490, compoundYield 37.9%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(racemic)-5-Bromo-3-[trans-2-(1-methylethyl)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]-1H-indole-7-carboxamide (60 mg, 0.145 mmol) was placed in a microwave vial and dissolved in 1,4-Dioxane (2 mL) and Water (1 mL). 3-Furanylboronic acid (16.24 mg, 0.145 mmol) and K2CO3 (60.2 mg, 0.435 mmol) were added. Argon was bubbled in the mixture for 10 mins, stirring. PdCl2(dppf) (5.60 mg, 0.012 mmol) was added, and argon was bubbled another 10 mins. The vial was sealed and put under microwave 5 mins at 100° C. with high absorption parameter. The crude was run through a thiol-SPE cartridge eluting with 2 mL of methanol and the eluted solvents are evaporated. The residue was dissolved in 2-3 mL of DMSO, filtered through a syringe filter (Acrodisc CR 13 mm; 45 um PTFE filter), and purified on a Gilson HPLC. The desired fractions were concentrated, giving 22 mg of the title compound.

Workup

  1. customArgon was bubbled in the mixture for 10 mins
  2. customargon was bubbled another 10 mins
  3. customThe vial was sealed
  4. washeluting with 2 mL of methanol
  5. customthe eluted solvents are evaporated
  6. dissolutionThe residue was dissolved in 2-3 mL of DMSO
  7. filtrationfiltered through a syringe
  8. filtrationfilter
  9. filtration(Acrodisc CR 13 mm; 45 um PTFE filter)
  10. custompurified on a Gilson HPLC
  11. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-9b5b8bfe69cf4280952008dcdc83343e
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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