Potassium Carbonate → HCID 67173431, compound

HRID 2036751Notes

Reaction equation

HRID 2036751 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[NH:15][C:14]4[CH2:19][CH:20]5[NH:24][CH:23]([C:13]=4[C:12]=3[C:11]=2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCC[C@H]1C(O)=O.I[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O.[Cu](I)I>[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:14]4[CH2:19][CH:20]5[NH:24][CH:23]([C:13]=4[C:12]=3[C:11]=2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]5)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 145742L-ProlineHCID 67085592HCID 67085592, compound

Product 1

HCID 67173431HCID 67173431, compoundYield 50.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of the product of step C (100 mg, 0.27 mmol) in dimethylsulfoxide (2 mL) was added copper iodide (51 mg, 0.02 mmol), L-proline (6.2 mg, 0.05 mmol), iodobenzene (33 μL, 0.29 mmol) and potassium carbonate (75 mg, 0.54 mmol). The resulting mixture was heated to 115° C. for 40 h, diluted with water and extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography (SiO2, 3:2 hexanes/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-5-phenyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (70 mg, 50%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.26 (s, 1H), 7.95-7.98 (m, 2H), 7.63 (d, J=8.7 Hz, 1H), 7.42-7.54 (m, 6H), 7.21-7.26 (m, 3H), 5.33 (br s, 1H), 4.65 (br s, 1H), 2.20-2.33 (m, 3H), 2.00-2.06 (m, 1H), 1.60-1.69 (m, 2H), 1.40 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (SiO2, 3:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d85955704efa4f548f36ab5cf67efb8c
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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