Acetic Acid → HCID 86628317, compound

HRID 21299Notes

Reaction equation

HRID 21299 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([C:24]2[N:25]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:26]3[C:31]([CH:32]=2)=[CH:30][C:29]([CH:33]=O)=[CH:28][CH:27]=3)=[C:18]2[C:14]=1[CH2:15][NH:16][C:17]2=[O:42])(=[O:11])=[O:10])#[N:2].[NH:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([C:24]2[N:25]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[C:26]3[C:31]([CH:32]=2)=[CH:30][C:29]([CH2:33][N:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:28][CH:27]=3)=[C:18]2[C:14]=1[CH2:15][NH:16][C:17]2=[O:42])(=[O:11])=[O:10])#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86628318HCID 86628318, compound

Product 1

HCID 86628317HCID 86628317, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-(2-cyanobenzenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.140 g, 0.238 mmol) was dissolved in acetonitrile (6.0 mL), and the solution was treated with pyrrolidine (0.398 mL, 4.77 mmol), acetic acid (0.273 mL, 4.77 mmol) and sodium triacetoxyborohydride (0.151 g, 0.715 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=85/15, 80/20) to obtain 4-(2-cyanobenzenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone (0.0773 g, ESI-MS m/z: 643 [M+H]+; 1H-NMR (CD3OD)8(ppm): 1.18 (s, 9H), 1.83-1.92 (m, 4H), 2.88-2.96 (m, 4H), 3.25 (s, 3H), 4.04 (s, 2H), 4.49 (s, 2H), 6.55 (s, 1H), 7.00 (s, 1H), 7.28 (dd, J=1.6, 8.7 Hz, 1H), 7.52 (d, J=1.6 Hz, 1H), 7.77-7.93 (m, 3H), 8.08 (dd, J=1.6, 7.3 Hz, 1H), 8.17 (d, J=8.7 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-8489ac5ad5d94c0a88917167d454d1cb
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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