Triethylamine → 3-Amino-4-phenyl-6-[1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-yl]phthalimide

HRID 20998Notes

Reaction equation

HRID 20998 reaction equation
[NH2:1][C:2]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10](Br)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[C:20]([O:24][C:25]([N:27]1[C:35]2[C:30](=[CH:31][C:32]([S:36]([N:39]3[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]3)(=[O:38])=[O:37])=[CH:33][CH:34]=2)[CH:29]=[C:28]1B(O)O)=[O:26])([CH3:23])([CH3:22])[CH3:21].CN1CCN(S(C2C=C3C(=CC=2)NC(B(O)O)=C3)(=O)=O)CC1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([C:28]2[N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[C:35]3[C:30]([CH:29]=2)=[CH:31][C:32]([S:36]([N:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)(=[O:37])=[O:38])=[CH:33][CH:34]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 573504271H-Indole-1-carboxylic acid, 2-borono-5-[(4-methyl-1-piperazinyl)sulfonyl]-, 1-(1,1-dimethylethyl) esterHCID 684900925-(4-methylpiperazin-1-ylsulfonyl)-1H-indol-2-boronic acidHCID 684918043-Amino-4-phenyl-6-bromophthalimide

Product 1

HCID 684894703-Amino-4-phenyl-6-[1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-yl]phthalimideYield 20.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

In a similar manner to Step 2 of Example 1, 3-amino-4-phenyl-6-bromophthalimide (70.0 mg, 0.221 mmol) was dissolved in acetonitrile (5.6 mL), and the solution was treated with a mixture (281 mg) of 1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-boronic acid synthesized in a similar manner to the literature [Bioorganic & Medicinal Chemistry Letters, 2004, vol. 14, p. 351] and 5-(4-methylpiperazin-1-ylsulfonyl)-1H-indol-2-boronic acid, palladium acetate (4.0 mg, 0.018 mmol), tri(o-tolyl)phosphine (11 mg, 0.035 mmol) and triethylamine (0.308 mL, 2.21 mmol), followed by purification by preparative thin-layer chromatography (ethyl acetate/methanol=20/1) to obtain Compound 2 (21 mg, yield 19%) and 3-amino-4-phenyl-6-[1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-yl]phthalimide (28 mg, yield 20%).

Workup

  1. customsynthesized in a similar manner to the literature [Bioorganic & Medicinal Chemistry Letters, 2004, vol. 14, p

Sources & evidence

ORD record
ord-4220ac8769d246598282898bcfd2be1a
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

Loading…