Triethylamine → 4-Trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

HRID 21193

Reaction equation

HRID 21193 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=[O:21])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].C(N(CC)CC)C.[F:37][C:38]([F:44])([F:43])[S:39](Cl)(=[O:41])=[O:40]>ClCCl>[F:37][C:38]([F:44])([F:43])[S:39]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=[O:21])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29])(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 866282304-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 866282874-Trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinoneYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 299, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (300 mg, 0.765 mmol) was dissolved in dichloromethane (12 mL), and the solution was treated with triethylamine (0.533 mL, 3.83 mmol) and trifluoromethanesulfonyl chloride (0.138 mL, 1.30 mmol) under ice-cooling, followed by purification by flash column chromatography (chloroform/methanol=100/0 to 98/2) to obtain 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (249 mg, yield 62%).

Workup

  1. temperaturecooling
  2. customfollowed by purification by flash column chromatography (chloroform/methanol=100/0 to 98/2)

Sources & evidence

ORD record
ord-bfa6f0fe4d774d85a7d7f634fdbc20f8
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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