Potassium Carbonate → HCID 86663027, compound

HRID 2410761Notes

Reaction equation

HRID 2410761 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=4)[CH:12]=[C:11]([C:25]([O:27][CH3:28])=[O:26])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[F:29][C:30]([F:45])([F:44])[S:31](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:22][C:21]([F:24])([F:23])[C:17]1[CH:16]=[C:15]([C:13]2[CH:12]=[C:11]([C:25]([O:27][CH3:28])=[O:26])[C:7]3[NH:8][C:9]4[CH:10]=[C:2]([O:1][S:31]([C:30]([F:45])([F:44])[F:29])(=[O:33])=[O:32])[CH:3]=[CH:4][C:5]=4[C:6]=3[N:14]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5498704-Nitrophenyl trifluoromethanesulfonateHCID 178497265HCID 178497265, compound

Product 1

HCID 86663027HCID 86663027, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of methyl 7-hydroxy-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (800 mg, 2.07 mmol), 4-nitrophenyl trifluoromethanesulfonate (842 mg, 3.11 mmol), and potassium carbonate (859 mg, 6.21 mmol) in DMF (12 ml) was stirred at RT for 3 hr. The reaction was partitioned between water and EtOAc. The organic phase was separated and washed with water (5×) and brine. It was dried with sodium sulfate and the solvent was removed. Column chromatography (step gradient elution with hexane containing 20 to 80% DCM) afforded methyl 2-(3-(trifluoromethyl)phenyl)-7-(trifluoromethylsulfonyloxy)-5H-pyrido[3,2-b]indole-4-carboxylate (548 mg, 1.06 mmol, 51% yield) as a light yellow solid. MS (ESI) m/z 587.09 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.76 (1H, s), 8.51 (1H, d, J=8.55 Hz), 8.44 (1H, s), 8.31-8.38 (2H, m), 7.60-7.72 (2H, m), 7.51 (1H, d, J=2.14 Hz), 7.29 (1H, dd, J=8.55, 2.14 Hz), 4.13 (3H, s).

Workup

  1. customThe reaction was partitioned between water and EtOAc
  2. customThe organic phase was separated
  3. washwashed with water (5×) and brine
  4. dry with materialIt was dried with sodium sulfate
  5. customthe solvent was removed
  6. washColumn chromatography (step gradient elution with hexane containing 20 to 80% DCM)

Sources & evidence

ORD record
ord-a03a85d1c7494bbd9ce4ce6dbef9438b
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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