4-(tert-Butyl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide → HCID 24756998, compound

HRID 557525Notes

Reaction equation

HRID 557525 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13](Br)[CH:14]=2)[CH:5]=[CH:4][CH:3]=1.[C:18]([C:22]1[CH:46]=[CH:45][C:25]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31](B3OC(C)(C)C(C)(C)O3)[C:30]=2[CH3:44])=[O:27])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>COCCOC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([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)=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([C:31]3[C:30]([CH3:44])=[C:29]([NH:28][C:26](=[O:27])[C:25]4[CH:24]=[CH:23][C:22]([C:18]([CH3:19])([CH3:20])[CH3:21])=[CH:46][CH:45]=4)[CH:34]=[CH:33][CH:32]=3)[CH:14]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 587289934-(tert-Butyl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamideHCID 597406173-(6-Amino-pyridin-2-ylamino)-5-bromo-1-methyl-1H-pyridin-2-one

Product 1

HCID 24756998HCID 24756998, compoundYield 40.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
95 °C

Procedure

A 48-mL sealed tube equipped with a magnetic stirring bar was charged with 3-(6-amino-pyridin-2-ylamino)-5-bromo-1-methyl-1H-pyridin-2-one (2) (0.054 g, 0.18 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (0.086 g, 0.22 mmol), and Pd(PPh3)4 (0.010 g, 0.010 mmol) in DME (10 mL) and 1N Na2CO3 (5 mL). After the mixture was degassed for 15 min., it was heated at 95° C. for 16 h. Then, the reaction mixture was cooled to room temperature and poured into H2O (10 mL). To this was added dichloromethane (10 mL) and the layers were separated. The aqueous phase was extracted with dichloromethane (3×10 mL), and the combined organic extracts were washed with H2O (5 mL) and brine (5 mL), dried (Na2SO4), and concentrated. The crude mixture was purified by column chromatography, gradient 0-10%, MeOH in dichloromethane/ether (1/1), to afford 0.035 g (40%) of N-{3-[5-(6-amino-pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl]-2-methyl-phenyl}-4-tert-butyl-benzamide (3) as a solid; LCMS m/z 482.2018 (M+).

Workup

  1. customA 48-mL sealed tube
  2. customequipped with a magnetic stirring bar
  3. customAfter the mixture was degassed for 15 min.
  4. temperatureThen, the reaction mixture was cooled to room temperature
  5. additionpoured into H2O (10 mL)
  6. additionTo this was added dichloromethane (10 mL)
  7. customthe layers were separated
  8. extractionThe aqueous phase was extracted with dichloromethane (3×10 mL)
  9. washthe combined organic extracts were washed with H2O (5 mL) and brine (5 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customThe crude mixture was purified by column chromatography, gradient 0-10%, MeOH in dichloromethane/ether (1/1)

Sources & evidence

ORD record
ord-725fb7a1c05c439480b4d0bdf3de71d5
Source dataset
uspto-grants-2011_11
Patent number
US08058446B2

Reaction notes

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