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

HRID 21194

Reaction equation

HRID 21194 reaction equation
FC(F)(F)S(O[C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH:25]=[O:26])=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:34])(=O)=O.[CH3:37]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC>[CH3:37][C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH:25]=[O:26])=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 866282874-Trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 866282884-Methyl-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinoneYield 86%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In a similar manner to Step 1 of Example 152, 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (176 mg, 0.336 mmol) was dissolved in dimethoxyethane (8.8 mL), and the solution was treated with trimethylboroxine (0.140 mL, 1.01 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (32.9 mg, 0.0403 mmol), potassium carbonate (231 mg, 1.68 mmol) and water (0.121 mL), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=4/1) to obtain 4-methyl-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (112 mg, yield 86%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=4/1)

Sources & evidence

ORD record
ord-e0bc7869ef5b4cfd9259b65a4d68cf53
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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