Phenylboronic Acid → HCID 59627869, compound

HRID 1256660Notes

Reaction equation

HRID 1256660 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18](Cl)[N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.C([O-])([O-])=O.[Na+].[Na+]>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 59627861HCID 59627861, compound

Product 1

HCID 59627869HCID 59627869, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of di-tert-butyl(6-chloro-3-nitropyridin-2-yl)imidodicarbonate (700 mg, 1.87 mmol), phenylboronic acid (274 mg, 2.25 mmol) and tetrakistriphenylphosphine palladium (217 mg, 0.187 mmol) were blanketed with argon and taken up in THF (15.0 mL) and 2M aq. Na2CO3 (3.74 mL). The suspension was purged with bubbling argon for 20 min, then the reaction was sealed and heated via microwave to 120° C. for 2 h. The reaction was cooled, diluted with EtOAc and filtered through celite. The filtrate was washed with water, brine, dried (MgSO4) and concentrated to afford material purified via MPLC, silica cartridge, 5-20% EtOAc in heptanes to afford the product as a light yellow solid. 1H NMR (DMSO-d6, 600 MHz) d 8.68 (d, J=8.5 Hz, 1H), 8.29 (d, J=8.5 Hz, 1H), 8.16-8.12 (m, 2H), 7.57-7.54 (m, 3H), 1.35 (s, 18H); MS cal'd 438 (M+Na)+, exp 438 (M+Na)+.

Workup

  1. customThe suspension was purged with bubbling argon for 20 min
  2. customthe reaction was sealed
  3. temperatureThe reaction was cooled
  4. additiondiluted with EtOAc
  5. filtrationfiltered through celite
  6. washThe filtrate was washed with water, brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto afford material
  10. custompurified via MPLC, silica cartridge, 5-20% EtOAc in heptanes

Sources & evidence

ORD record
ord-aecdcfb6f4d946cb84d8941e4ff054b7
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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