Potassium Carbonate → HCID 52933352, compound

HRID 1423075Notes

Reaction equation

HRID 1423075 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][N:16]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[C:17]=3[CH:18]=[C:19]([C:21]#[N:22])[CH:20]=2)=[O:11])=[CH:4][CH:3]=1.[CH3:30][S:31]([NH2:34])(=[O:33])=[O:32].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O.CN1C(=O)CCC1>[CH3:30][S:31]([NH:34][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][N:16]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[C:17]=3[CH:18]=[C:19]([C:21]#[N:22])[CH:20]=2)=[O:11])=[CH:4][CH:3]=1)(=[O:33])=[O:32]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86672836HCID 86672836, compound

Product 1

HCID 52933352HCID 52933352, compound

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of 6-cyano-1-(4-fluorophenyl)-1H-indole-4-carboxylic acid (6-bromo-pyridin-3-ylmethyl)-amide (75 mg, 0.17 mmol), methanesulfonamide (81 mg, 0.85 mmol), copper (II) trifluoromethanesulfonate (105 mg, 0.290 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (55.2 μL, 0.35 mmol) and potassium carbonate (247 mg, 1.79 mmol) in a sealed tube is added NMP (2.5 mL). The solution is degassed with argon for 3 minutes. The reaction is warmed at 125° C. in a microwave reactor. After 40 minutes, the reaction is diluted with saturated aqueous potassium carbonate (15 mL) and extracted with EtOAc (2×15 mL). The combined organic layers are washed with brine (2×15 mL), dried over magnesium sulfate and concentrated in vacuo. The residue is purified by preparative reversed phase HPLC to afford the title compound.

Workup

  1. customThe solution is degassed with argon for 3 minutes
  2. additionthe reaction is diluted with saturated aqueous potassium carbonate (15 mL)
  3. extractionextracted with EtOAc (2×15 mL)
  4. washThe combined organic layers are washed with brine (2×15 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-f78fcd3bd3f24016a15c3b391584d1ec
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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