Tetrahydrofuran → 5-Benzyl-2-methoxypyridine

HRID 2075216Notes

Reaction equation

HRID 2075216 reaction equation
CO[C:3]1[CH:4]=[CH:5][CH:6]=[C:7](OC)[C:8]=1[C:9]1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:39]1[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[N:43][CH:44]=1.C(B1C2CCCC1CCC2)C1C=CC=CC=1.C1COCC1>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:9]([C:39]1[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[N:43][CH:44]=1)[C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 27348955-Bromo-2-methoxypyridineHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 584153415-Benzyl-2-methoxypyridine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A sealable tube was charged with S-phos (0.22 g, 0.53 mmol), palladium acetate (0.060 g, 0.27 mmol), potassium phosphate (8.5 g, 40 mmol) and 5-bromo-2-methoxypyridine (1.8 mL, 13 mmol) under argon. 9-Benzyl-9-bora-bicyclo[3.3.1]nonane 0.5M in THF (53 mL, 27 mmol) was added, the vessel was sealed and heated to 60° C. overnight. The mixture was diluted with diethyl ether and was filtered through a pad of celite. Evaporation of the filtrate and purification by flash chromatography (0-40% EtOAc/hexanes) gave 5-benzyl-2-methoxypyridine. MS (ESI) m/z: Calculated: 199.1; Observed: 200.1 (M++1).

Workup

  1. customthe vessel was sealed
  2. filtrationwas filtered through a pad of celite
  3. customEvaporation of the filtrate and purification by flash chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5a2f00f4c2dc4180bd15b5ddf031ef9d
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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