Triethylamine → 4-(2-Trifluoromethyl-5-methyl-3-furansulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21155Notes

Reaction equation

HRID 21155 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].C(N(CC)CC)C.[CH3:42][C:43]1[O:47][C:46]([C:48]([F:51])([F:50])[F:49])=[C:45]([S:52](Cl)(=[O:54])=[O:53])[CH:44]=1>C(#N)C>[F:51][C:48]([F:49])([F:50])[C:46]1[O:47][C:43]([CH3:42])=[CH:44][C:45]=1[S:52]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34])(=[O:54])=[O:53]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27798955-methyl-2-(trifluoromethyl)furan-3-sulfonyl ChlorideHCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 866282604-(2-Trifluoromethyl-5-methyl-3-furansulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneYield 23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 1 of Example 233, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0277 g, 0.0600 mmol) was dissolved in acetonitrile (0.650 mL), and the solution was treated with triethylamine (0.0540 mL, 0.390 mmol) and 5-methyl-2-trifluoromethyl-3-furansulfonyl chloride (0.0486 g, 0.195 mmol) to obtain 4-(2-trifluoromethyl-5-methyl-3-furansulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0092 g, yield 23%).

Sources & evidence

ORD record
ord-51e393bd984b4295a26b2d6abdfee449
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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