Sodium Carbonate → (+/-)-3-{4-[4-(2-Methyl-piperidin-1-ylmethyl)-oxazol-2-yl]-phenyl}-pyridine

HRID 1445793Notes

Reaction equation

HRID 1445793 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]3[CH3:20])[N:12]=2)=[CH:4][CH:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][N:14]1[CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)=[CH:3][CH:4]=2)[O:9][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11508283HCID 11508283, compound

Product 1

HCID 11537304(+/-)-3-{4-[4-(2-Methyl-piperidin-1-ylmethyl)-oxazol-2-yl]-phenyl}-pyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-[2-(4-Bromo-phenyl)-oxazol-4-ylmethyl]-2-methyl-piperidine (See Example 21) (1.0 mmol; N96-A03858-154), 3-pyridyl boronic acid (1.2 mmol), tetrakis-(triphenylphosphine)palladium (0.044 mmol), 2M aqueous sodium carbonate (3 mmol) and dioxane (0.1M) is placed in a microwave reactor vessel with a stirbar. Run the reaction in a CEM microwave reactor at 90° C. with 30 W power and cooling for 30 minutes. After this time, perform an aqueous workup and purify via radial chromatography eluting with 2M ammonia in methanol and dichloromethane to provide the titled compound. MS (m/e): 334.2 (M+1)

Workup

  1. customthe reaction in a CEM microwave reactor at 90° C. with 30 W power
  2. temperaturecooling for 30 minutes
  3. custompurify via radial chromatography
  4. washeluting with 2M ammonia in methanol and dichloromethane

Sources & evidence

ORD record
ord-7c9e3552d7144e4e8dbc6595ff67d43a
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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