Potassium Carbonate → HCID 57732732, compound

HRID 1806315Notes

Reaction equation

HRID 1806315 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][N:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+].[CH3:37][N:38]([CH3:48])[C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1>O>[CH3:37][N:38]([CH3:48])[C:39]1[CH:44]=[CH:43][C:42]([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[CH:14]2[CH2:15][CH2:16][N:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH2:18][CH2:19]2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343444-(Dimethylamino)phenylboronic acidHCID 113844275-bromo-3-[1-(ethanesulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 57732732HCID 57732732, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a CEM microwave tube was added 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (40 mg, 0.097 mmol), dioxane (2.8 mL) and a solution of potassium carbonate (40 mg, 0.289 mmol) in water (1.2 mL). To this mixture was added [4-(dimethylamino)phenyl]boronic acid (65 mg, 0.386 mmol) and chloro-2-(dimethylaminormethyl)-ferrocen-1-yl-(dinorbornylphosphine)palladium(II) (1 mg, 0.002 mmol). The vial was capped and the reaction was reacted in a CEM microwave for 10 min at 160° C. The reaction was concentrated under a stream of nitrogen at 80° C. The crude product was taken up in dimethyl sulfoxide (1 mL) and purified through a 1 g silica SPE cartridge eluting with dimethyl sulfoxide (4 mL). The dimethyl sulfoxide was concentrated in a Genevac at 65° C. for 3 h, and the residue was reconstituted in dimethyl sulfoxide (1 mL) and filtered through an acrodisc. The solution of crude product was then purified on the Agilent MDAP (UV 214 selection). The purified product was passed through a polymer-bound carbonate SPE cartridge to afford 2.7 mg of the title compound (6.2%).

Workup

  1. customThe vial was capped
  2. customthe reaction was reacted in a CEM microwave for 10 min at 160° C
  3. concentrationThe reaction was concentrated under a stream of nitrogen at 80° C
  4. custompurified through a 1 g silica SPE cartridge
  5. washeluting with dimethyl sulfoxide (4 mL)
  6. concentrationThe dimethyl sulfoxide was concentrated in a Genevac at 65° C. for 3 h
  7. filtrationfiltered through an acrodisc
  8. customThe solution of crude product was then purified on the Agilent MDAP (UV 214 selection)

Sources & evidence

ORD record
ord-4e768f2f1bf8498db28d8fb27123a383
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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