Triethylamine → HCID 86628303, compound

HRID 21287

Reaction equation

HRID 21287 reaction equation
[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12](I)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:18])(=[O:4])=[O:3].[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1B(O)O)=[O:25])([CH3:22])([CH3:21])[CH3:20].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>[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:27]2[N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[C:34]3[C:29]([CH:28]=2)=[CH:30][CH:31]=[CH:32][CH:33]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:18])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 768469524-Methanesulfonyloxy-5-methoxy-7-iodoisoindolinone

Product 1

HCID 86628303HCID 86628303, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 1, 4-methanesulfonyloxy-5-methoxy-7-iodoisoindolinone (50.0 mg, 0.130 mmol) was dissolved in acetonitrile (3 mL), and the solution was treated with 1-(tert-butoxycarbonyl)indole-2-boronic acid (68.1 mg, 0.261 mmol), palladium acetate (2.3 mg, 0.010 mmol), tri(o-tolyl)phosphine (6.3 mg, 0.021 mmol) and triethylamine (0.181 mL, 1.30 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=7/3 to 1/1 to 3/7) to obtain 4-methanesulfonyloxy-5-methoxy-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinone (56.9 mg, yield 93%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=7/3 to 1/1 to 3/7)

Sources & evidence

ORD record
ord-3fb38c07ba17448c95fa500dea46ca91
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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