Water → HCID 49803416, compound

HRID 1020396Notes

Reaction equation

HRID 1020396 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:32])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[C:23]=3Br)[C:18]2=[O:31])=[CH:12][CH:11]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C(OCC)(=O)C.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:32])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[C:23]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:18]2=[O:31])=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 49803415HCID 49803415, compound

Product 1

HCID 49803416HCID 49803416, compoundYield 92.9%

Reagents, catalysts & solvents 3

HCID 178420554HCID 178420554, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(2-aminophenyl)-4-((4-bromo-5,6-dimethoxy-1-oxoisoindolin-2-yl)methyl)benzamide (60 mg, 0.12 mmol) in Example 1, phenyl boronic acid (22 mg, 0.18 mmol, 1.5 equiv.), tetrakis(triphenyl-phosphino)palladium (8.4 mg, 0.0073 mmol, 6 mol %) and sodium carbonate (38 mg, 0.36 mmol, 3 equiv.) were dissolved in a mixture of dioxane and the distilled water (mixture ratio=4:1 (v/v), 5.0 mL) and the resulting solution was reacted at 150° C. under microwave for 15 mins. The resulting material thus obtained was diluted with ethyl acetate (EtOAc), dried over anhydrous MgSO4, and filtered with Celite. The filtrates were distilled under a reduced pressure to remove the solvent and the resulting residue was subjected to a silica gel column chromatography (EtOAc) to obtain the title compound (55 mg, 92%).

Workup

  1. customThe resulting material thus obtained
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered with Celite
  4. distillationThe filtrates were distilled under a reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-66f0c7349f9745b4ba79247b8841e527
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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