Potassium Carbonate → HCID 67985009, compound

HRID 705386Notes

Reaction equation

HRID 705386 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[C:10]2[CH:11]=[C:12]([O:29][CH:30]([CH3:32])[CH3:31])[C:13]([N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][C:9]=2[O:8][C:7]=1[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CS(C)=O.C(OCC)(=O)C>[F:39][C:36]1[CH:35]=[CH:34][C:33]([C:7]2[O:8][C:9]3[CH:14]=[C:13]([N:15]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[S:16]([CH3:19])(=[O:18])=[O:17])[C:12]([O:29][CH:30]([CH3:32])[CH3:31])=[CH:11][C:10]=3[C:6]=2[C:2]2[NH:3][CH:4]=[CH:5][N:1]=2)=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 12217721Iodo benzene diacetate2×HCID 86710160HCID 86710160, compound

Product 1

HCID 67985009HCID 67985009, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-fluorophenyl)-5-isopropoxybenzofuran-6-yl)-N-(4-methoxybenzyl)methanesulfonamide (0.54 g, 0.98 mmol) was dissolved in dimethylsulfoxide (5 mL) and was treated with potassium carbonate (0.15 g, 1.08 mmol) and iodobenzene diacetate (0.35 g, 1.08 mmol). The initially yellow solution changed to a reddish-brown solution within 15 minutes of iodobenzene diacetate addition. The reaction mixture was stirred for one hour at room temperature. The reaction mixture was stirred with 50 mL ethyl acetate and 50 mL 10% aqueous sodium bicarbonate for 20 minutes, the layers were separated and the aqueous layer was extracted with 50 mL additional ethyl acetate. The combined organic extracts were washed with 10% aqueous sodium chloride, dried over anhydrous sodium sulfate(s), and filtered. The solvent was removed in vacuo leaving an orange oily residue, which was purified by reverse phase HPLC yielding an off-white solid. 40 mg, 7.4%. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (d, 6H) 3.13 (s, 3H) 3.67 (s, 3H) 4.37-5.02 (m, 3H) 6.73-6.92 (m, 2H) 7.06-7.22 (m, 4H) 7.22-7.41 (m, 4H) 7.79-7.98 (m, 2H) 12.37 (s, 1H); MS (ESI+) m/z 550.2 (M+H)+, MS (ESI−) m/z 548.1.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with 50 mL additional ethyl acetate
  3. washThe combined organic extracts were washed with 10% aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate(s)
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customleaving an orange oily residue, which
  8. customwas purified by reverse phase HPLC
  9. customyielding an off-white solid

Sources & evidence

ORD record
ord-8d5de6961d8b454ea0059adb5b15435f
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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