Cesium carbonate → 2-Chloro-4-methoxy-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine

HRID 1959610Notes

Reaction equation

HRID 1959610 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6](F)[CH:5]=[CH:4][N:3]=1.BrC1C=NC=C(Cl)C=1[CH2:24][O:25]C1CCCCO1.C([O-])([O-])=O.[Cs+].[Cs+]>CO>[Cl:1][C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6]([O:25][CH3:24])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 44190473HCID 44190473, compoundHCID 866453642-Chloro-4-fluoro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine

Product 1

HCID 866453632-Chloro-4-methoxy-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-chloro-4-fluoro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (0.20 g. 0.81 mmol) which was prepared according to the synthesis of 3-bromo-5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine in anhydrous MeOH (4 mL) was added Cs2CO3 (0.54 g. 1.6 mmol). After vigorous stirring for 20 h at room temperature acedic acid (92 μL. 1.6 mmol) was added the solvent was removed in vacuo and the residue was partitioned between DCM (20 mL) and water (4 mL). The organic layer was dried over Na2SO4 filtered and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 257.9 [M+H+].

Workup

  1. additionwas added the solvent
  2. customwas removed in vacuo
  3. customthe residue was partitioned between DCM (20 mL) and water (4 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-08b5f9dc8262426c8a69112e9dc8110e
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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