Triethylamine → HCID 86628323, compound

HRID 21304Notes

Reaction equation

HRID 21304 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([C:13]2[N:14]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:36].C(N(CC)CC)C.[F:44][C:45]1[CH:46]=[C:47]([S:52](Cl)(=[O:54])=[O:53])[CH:48]=[CH:49][C:50]=1[CH3:51]>C(#N)C>[F:44][C:45]1[CH:46]=[C:47]([S:52]([O:1][C:2]2[C:10]([O:11][CH3:12])=[CH:9][C:8]([C:13]3[N:14]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C:15]4[C:20]([CH:21]=3)=[CH:19][C:18]([CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:17][CH:16]=4)=[C:7]3[C:3]=2[CH2:4][NH:5][C:6]3=[O:36])(=[O:54])=[O:53])[CH:48]=[CH:49][C:50]=1[CH3:51]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27786003-Fluoro-4-methylbenzene-1-sulfonyl chlorideHCID 684937934-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 86628323HCID 86628323, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 1 of Example 227, 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.188 g, 0.382 mmol) was dissolved in acetonitrile (8.0 mL), and the solution was treated with triethylamine (0.160 mL, 1.15 mmol) and 3-fluoro-4-methylbenzenesulfonyl chloride (0.120 mg, 0.574 mmol) to obtain 4-(3-fluoro-4-methylbenzenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0690 g, yield 27%).

Sources & evidence

ORD record
ord-3cc9b3bfd56741858bc8eaf063b956e5
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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