Potassium Carbonate → HCID 24830316, compound

HRID 1025360Notes

Reaction equation

HRID 1025360 reaction equation
[CH:1]([C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[CH:11][CH:10]=1)=[O:2].S([CH2:36][N+:37]#[C-:38])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CO>[O:2]1[C:1]([C:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]3[C:18]([F:24])=[CH:19][CH:20]=[CH:21][C:22]=3[F:23])=[CH:11][CH:10]=2)=[CH:38][N:37]=[CH:36]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 59517949HCID 59517949, compound

Product 1

HCID 24830316HCID 24830316, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of Compound 100 (60 mg, 0.17 mmol), tosylmethylisocyanide (38 mg, 0.19 mmol) and K2CO3 (50 mg, 0.36 mmol) in MeOH (5 mL) were heated at 90° C. for 40 min before it was filtered and concentrated. The residue was dissolved in EtOAc (10 mL) and H2O (10 mL). The organic phase was collected, dried and concentrated. Column chromatography afforded Compound 23 (47, 65%). 1H NMR (300 MHz, CDCl3) δ 7.64-7.59 (m, 4H), 7.46-7.40 (m, 1H), 7.12 (d, J=8.7 Hz, 2H), 7.01 (t, J=8.1 Hz, 2H), 6.21 (s, 1H), 2.49-2.40 (m, 4H), 1.84-1.76 (m, 4H);

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (10 mL)
  4. customThe organic phase was collected
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f0e800a585df49e9bc5b87e12507f687
Source dataset
uspto-grants-2014_05
Patent number
US08729069B2

Reaction notes

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