Triethylamine → HCID 86628298, compound

HRID 21278Notes

Reaction equation

HRID 21278 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[N:13]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35].C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>ClCCl>[CH3:43][S:44]([O:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[N:13]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35])(=[O:46])=[O:45]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 684899824-Hydroxy-5-methyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 86628298HCID 86628298, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 289, 4-hydroxy-5-methyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (80.5 mg, 0.170 mmol) was dissolved in dichloromethane (3 mL), and the solution was treated with triethylamine (0.095 mL, 0.68 mmol) and methanesulfonyl chloride (0.026 mL, 0.34 mmol), followed by purification by slurry using hexane to obtain 4-methanesulfonyloxy-5-methyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (80.3 mg, yield 85%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-439c907de8a64e048c5913f20ddf1b66
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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