Nitrogen → 4-(4-(Benzyloxy)phenyl)pyridine

HRID 393281Notes

Reaction equation

HRID 393281 reaction equation
N#N.[C:3]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br.Br[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N.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>[C:3]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 446301274-Bromopyridine Hydrobromide

Product 1

HCID 226488624-(4-(Benzyloxy)phenyl)pyridineYield 94.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Pd(PPh3)4 (10.0 mg, 0.01 mmol) was added to a degassed (N2) mixture of 4-(phenylmethoxy)phenylboronic acid (230 mg, 1.01 mmol), 4-bromopyridine hydrobromide (194 mg, 1.00 mmol), aqueous 1 M Na2CO3 solution (4.0 mL) in MeCN (4 mL). The reaction mixture was heated to 85° C. for 5 h. The cooled suspension was filtered and the resulting solid was washed with aqueous MeCN. The filtrate was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc) and combined with the solid obtained by filtration to give the title compound (247 mg, 94% yield) as a white solid.

Workup

  1. customa degassed
  2. filtrationThe cooled suspension was filtered
  3. washthe resulting solid was washed with aqueous MeCN
  4. extractionThe filtrate was extracted with CH2Cl2
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (EtOAc)
  9. customobtained by filtration

Sources & evidence

ORD record
ord-c7a3cee2087e448db58a25c55f14ab36
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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