Water → HCID 20767729, compound

HRID 984848Notes

Reaction equation

HRID 984848 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].Br[C:25]1[N:29]([CH3:30])[CH:28]=[N:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.CCO.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>[CH3:1][O:2][C:3]([C:5]1[C:14]([C:25]2[N:29]([CH3:30])[CH:28]=[N:27][CH:26]=2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 22285041HCID 22285041, compound

Product 1

HCID 20767729HCID 20767729, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a mixture of methyl-3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate (Preparation 13) (15.37 g, 49.3 mmol) and 5-bromo-1-methyl-1H-imidazole (9.06 g, 49.3 mmol) in toluene/EtOH (350 mL/36 mL) were added Pd(PPh3)4 (11.37 g, 9.84 mmol), Na2CO3 (20.9 g, 197.2 mmol) and water (106 mL). The mixture was degassed, purged with N2, and heated to reflux for 20 hours. It was then cooled to RT, neutralized with HCl (1.0 N, 100 mL), and concentrated in vacuo. The residue was partitioned between water (300 mL) and EtOAc (1 L). The organic layer was washed with water (2 L) and brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting crude material was submitted to flash chromatography (1.5% MeOH/CHCl3), furnishing the title compound as a light-yellow solid (9.5 g, 72%). 1H NMR (CDCl3): 8.53 (s, 1H), 7.99 (d, J=8.1, 1H), 7.80 (d, J=8.1, 1H), 7.77 (s, 1H), 7.56 (m, 1H), 7.54 (m, 1H), 7.54 (s, 1H), 6.94 (s, 1H), 3.73 (s, 3H), 3.29 (s, 3H). (ESI) m/z (M+H)+=267.11.

Workup

  1. customThe mixture was degassed
  2. custompurged with N2
  3. temperatureheated
  4. temperatureto reflux for 20 hours
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between water (300 mL) and EtOAc (1 L)
  7. washThe organic layer was washed with water (2 L) and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-9a79fa7065e548a28a4cf951f817df57
Source dataset
uspto-grants-2005_03
Patent number
US06869956B2

Reaction notes

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