Potassium Carbonate → HCID 54381333, compound

HRID 1870969Notes

Reaction equation

HRID 1870969 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[C:5]2[CH2:20][C@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[CH3:26].I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[CH3:26][N:22]1[CH2:23][CH2:24][CH2:25][C@@H:21]1[CH2:20][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:3]=2)[N:7]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 53933380HCID 53933380, compound

Product 1

HCID 54381333HCID 54381333, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (R)-5-hydroxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole (Example 10, 74 mg, 0.20 mmol) and iodobenzene (61.2 mg, 0.3 mmol) with K2CO3 (41.4 mg 0.30 mmol), CuBr (17.2 0.12 mmol) and Cu powder (10 mg, 0.15 mmol) in NMP (0.7 mL) was heated at 170° C. Aqueous workup and flash chromatography (silica gel) yielded (R)-3-(1-methyl-2-pyrrolidinylmethyl)5-phenoxy-1-phenylsulfonylindole (5.8 mg, 8%, HRMS-FAB+ : C26H26N2O3S, calculated MH+ :447.17422; found MH+ : 447.17240).

Sources & evidence

ORD record
ord-30ccd657d0e44946be015c3279d52aae
Source dataset
uspto-grants-2000_08
Patent number
US06100291

Reaction notes

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