Acetic Acid → HCID 86628326, compound

HRID 21306Notes

Reaction equation

[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH:26]=O)[CH:22]=[CH:21][CH:20]=3)=[C:11]2C=1CN[C:10]2=[O:35])(=[O:4])=[O:3].[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:59](#[N:61])[CH3:60]>>[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH2:26][N:38]([CH2:39][CH3:40])[CH2:36][CH3:37])[CH:22]=[CH:21][CH:20]=3)=[C:11]2[C:60]=1[CH2:59][NH:61][C:10]2=[O:35])(=[O:4])=[O:3]

Participants

Reactant 5

HCID 176Acetic Acid

HCID 6342Acetonitrile

HCID 8021Diethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 866283254-Methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-formylindol-2-yl]isoindolinone

Product 1

HCID 86628326HCID 86628326, compoundYield 57%

Procedure

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-formylindol-2-yl]isoindolinone (0.226 g, 0.452 mmol) was dissolved in acetonitrile (15.0 mL) and the solution was treated with diethylamine (0.935 mL, 9.03 mmol), acetic acid (0.517 mL, 9.03 mmol) and sodium triacetoxyborohydride (0.479 g, 2.26 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=3/1) to obtain 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-(diethylaminomethyl)indol-2-yl]isoindolinone (0.144 g, 57%).

Workup

customfollowed by purification of the residue by flash column chromatography (chloroform/methanol=3/1)

Sources & evidence

ORD record: ord-d869d32971364482a916dc88fae8025d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Reaction notes

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