Potassium Carbonate → HCID 59332600, compound

HRID 387374Notes

Reaction equation

HRID 387374 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[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[C:16]([CH3:23])([CH3:22])[CH2:15]1.O1[CH2:29][CH2:28]OCC1.C([O-])([O-])=O.[K+].[K+]>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>[CH3:22][C:16]1([CH3:23])[CH2:15][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:28]=[CH:9][CH:10]=[CH:2][CH:3]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:19][CH2:18][S:17]1(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 59332724HCID 59332724, compound

Product 1

HCID 59332600HCID 59332600, compoundYield 18%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

5-Bromo-3-(2,2-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (104 mg, 0.26 mmol) was placed in a microwave vial and dissolved with 1,4-dioxane (6 mL) and water (3 mL). 3-Phenylboronic acid (64 mg, 0.52 mmol) and K2CO3 (108 mg, 0.78 mmol) were added. Argon was bubbled in the mixture for 10 min with stirring. PdCl2(dppf) (10 mg, 0.02 mmol) was added, and argon was bubbled another 10 min. The vial is sealed and heated in a microwave for 5 min at 100° C. on high absorption. The reaction was evaporated to remove most of the dioxane. The residue was partitioned between ethyl acetate and water. The layers were separated, the organic layer was dried (MgSO4), and the solvent was removed under vacuum. The residue was dissolved in DMSO (3 mL), and was purified on a Gilson HPLC. The desired fractions were concentrated, giving 20 mg (18%) of the title compound.

Workup

  1. customArgon was bubbled in the mixture for 10 min
  2. customargon was bubbled another 10 min
  3. customThe vial is sealed
  4. customThe reaction was evaporated
  5. customto remove most of the dioxane
  6. customThe residue was partitioned between ethyl acetate and water
  7. customThe layers were separated
  8. dry with materialthe organic layer was dried (MgSO4)
  9. customthe solvent was removed under vacuum
  10. dissolutionThe residue was dissolved in DMSO (3 mL)
  11. customwas purified on a Gilson HPLC
  12. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-77aac018b88149d7a78a6304c7ca8583
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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