Triethylamine → HCID 86628333, compound

HRID 21327Notes

Reaction equation

HRID 21327 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH:13]2[O:15][CH2:14]2)=[CH:9][C:8]([C:16]2[N:17]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:18]3[C:23]([C:24]=2C)=[CH:22][C:21]([CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:20][CH:19]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:40].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH:13]2[O:15][CH2:14]2)=[CH:9][C:8]([C:16]2[N:17]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:26][N:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)=[CH:20][CH:19]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 86628334HCID 86628334, compound

Product 1

HCID 86628333HCID 86628333, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 1, 4-chloro-5-(2,3-epoxypropoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)methylindol-2-yl]isoindolinone (77.1 mg, 0.211 mmol) was dissolved in acetonitrile (2.3 mL), and the solution was treated with Compound BD (151 mg, 0.383 mmol), palladium acetate (3.8 mg, 0.017 mmol), tri(o-tolyl)phosphine (10.3 mg, 0.034 mmol) and triethylamine (0.294 mL, 2.11 mmol), followed by purification by slurry using diisopropylether to obtain 4-chloro-5-(2,3-epoxypropoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (92.3 mg, yield 79%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-8fea3c4c6ffe499394ed5213d46d0204
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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