Acetic Acid → HCID 86628314, compound

HRID 21297Notes

Reaction equation

HRID 21297 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.Cl.[CH3:41][NH:42][CH3:43].C(N(CC)CC)C.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]([CH3:36])([CH3:38])[CH3:37])=[O:33])[C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([CH2:30][N:42]([CH3:43])[CH3:41])=[CH:25][CH:24]=4)=[C:15]3[C:11]=2[CH2:12][NH:13][C:14]3=[O:39])(=[O:7])=[O:8])=[CH:2]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 86628315HCID 86628315, compound

Product 1

HCID 86628314HCID 86628314, compoundYield 45.2%

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 (0.219 g, 0.385 mmol) was dissolved in acetonitrile (6.0 mL), and the solution was treated with dimethylamine hydrochloride (0.630 g, 7.70 mmol), triethylamine (1.10 mL, 7.70 mmol), acetic acid (0.441 mL, 7.70 mmol) and sodium triacetoxyborohydride (0.245 g, 1.16 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=85/15) to obtain 4-(3-thiophenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone (0.104 g, 45%).

Workup

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

Sources & evidence

ORD record
ord-8dab93f7cf6a41df872f0c4e68a17dc8
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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