Potassium Carbonate → HCID 59332671, compound

HRID 656154Notes

Reaction equation

HRID 656154 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[CH2:30][CH2:29]O[CH2:27][CH2:26]1.O1C=CC=C1B(O)O.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>[O:25]1[CH:30]=[CH:29][CH:27]=[C:26]1[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]([CH3:23])[CH3:24])[CH2:15]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2734357Furan-2-boronic acidHCID 66746207HCID 66746207, compound

Product 1

HCID 59332671HCID 59332671, compound

Reagents, catalysts & solvents 2

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

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 with 1,4-Dioxane (2 mL) and Water (1 mL). 2-Furanylboronic acid (33 mg, 0.29 mmol) and K2CO3 (60 mg, 0.44 mmol) were added. Argon was bubbled into 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 brown oil was dissolved in 2-3 mL of DMSO, and on a Gilson HPLC. The desired fractions were concentrated, giving 32 mg of the title compound.

Workup

  1. customArgon was bubbled into 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 brown oil was dissolved in 2-3 mL of DMSO
  7. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-d4b70674d342400f93232dee89dcb425
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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