Acetic Acid → HCID 86628316, compound

HRID 21298Notes

Reaction equation

HRID 21298 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([S:6]([O:9][C:10]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]3[N:22]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([CH:30]=O)=[CH:25][CH:24]=4)=[C:15]3[C:11]=2[CH2:12][NH:13][C:14]3=[O:39])(=[O:8])=[O:7])=[CH:2]1.[NH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[S:1]1[CH:5]=[CH:4][C:3]([S:6]([O:9][C:10]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]3[N:22]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([CH2:30][N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:25][CH:24]=4)=[C:15]3[C:11]=2[CH2:12][NH:13][C:14]3=[O:39])(=[O:8])=[O:7])=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86628315HCID 86628315, compound

Product 1

HCID 86628316HCID 86628316, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-(3-thiophenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.0650 g, 0.114 mmol) was dissolved in acetonitrile (5.0 mL), and the solution was treated with pyrrolidine (0.191 mL, 2.29 mmol), acetic acid (0.131 mL, 2.29 mmol) and sodium triacetoxyborohydride (0.0730 g, 0.343 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=85/15, 80/20) to obtain 4-(3-thiophenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone (0.0501 g, 70%).

Workup

  1. customfollowed by purification of the residue by flash column chromatography (chloroform/methanol=85/15, 80/20)

Sources & evidence

ORD record
ord-87513aa9ebed4eb5b9411e8ae8acbf16
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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