Ammonium → HCID 66746783, compound

HRID 387395Notes

Reaction equation

HRID 387395 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])[CH:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15]1.O1[CH2:33][CH2:32]OCC1.O.[NH4+]>CS(C)=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:20]=[S:17]1(=[O:21])[CH2:18][CH2:19][CH:14]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:33]4[CH:32]=[CH:9][CH:10]=[CH:2][CH:3]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15][CH:16]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 223AmmoniumHCID 962WaterHCID 312751,4-DioxaneHCID 59332714HCID 59332714, compound

Product 1

HCID 66746783HCID 66746783, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

5-Bromo-3-(1,1-dioxido-2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (100 mg, 0.224 mmol) was placed in a microwave vial and combined with 1,4-Dioxane (3 mL) and Water (1.5 mL). Argon was bubbled through the mixture for 10 mins, stirring and then PdCl2(dppf) (8.18 mg, 0.011 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 evaporated to remove the most of the dioxane. Then it was partitioned between EtOAc and water. Organic layer was dried over magnesium sulfate and solvent removed under vacuum to afford 155 mg of crude material as a gummy brown oil which was dissolved in 1-2 mL of DMSO, and run through the ammonium Gilson to afford 17 mg of (racemic)-3-(1,1-dioxido-2-phenyltetrahydro-2H-thiopyran-4-yl)-5-phenyl-1H-indole-7-carboxamide.

Workup

  1. customArgon was bubbled through the mixture for 10 mins
  2. customargon was bubbled another 10 mins
  3. customThe vial was sealed
  4. customThe crude was evaporated
  5. customto remove the most of the dioxane
  6. customThen it was partitioned between EtOAc and water
  7. dry with materialOrganic layer was dried over magnesium sulfate and solvent
  8. customremoved under vacuum
  9. customto afford 155 mg of crude material as a gummy brown oil which

Sources & evidence

ORD record
ord-c908ce25e06f4517a6ed70b1d6ae67e3
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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