Sodium Carbonate → HCID 68539388, compound

HRID 1992865Notes

Reaction equation

HRID 1992865 reaction equation
Br[C:2]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][CH3:16])[CH:8]=2)[C:3]=1[O:17][CH2:18][O:19][CH3:20].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.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.COCCOC>[CH3:13][CH:12]([C:11]1[C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:3]([O:17][CH2:18][O:19][CH3:20])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:15][CH3:16])=[CH:6][CH:5]=2)[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68537262HCID 68537262, compound

Product 1

HCID 68539388HCID 68539388, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
160 °C

Procedure

A sealed tube containing 2-bromo-3-(1-methylethyl)-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}naphthalene (70) (0.24 g, 0.71 mmol), phenyl boronic acid (0.18 g, 1.41 mmol), Pd(PPh3)4 (82 mg, 0.07 mmol), 2 M Na2CO3 (5 mL) and DME (5 mL) was heated at 160° C. for 20 min. Cooled to room temperature, the mixture was extracted with ether (2×50 mL). The organic extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (25:1) to give 0.23 g (97%) of compound 71 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.16 (d, J=6.8 Hz, 6H), 2.92 (sept, J=6.8 Hz, 1H), 3.06 (s, 3H), 3.93 (s, 3H), 4.71 (s, 2H), 7.08-7.15 (m, 2H), 7.30-7.40 (m, 3H), 7.40-7.46 (m, 2H), 7.52 (s, 1H), 8.01 (d, J=9.0 Hz, 1H).

Workup

  1. temperatureCooled to room temperature
  2. extractionthe mixture was extracted with ether (2×50 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as a yellow oil
  8. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (25:1)

Sources & evidence

ORD record
ord-92550b1efa774c84898e912d39cc8450
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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