Methanol → HCID 68736834, compound

HRID 1878629Notes

Reaction equation

HRID 1878629 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[N:6][CH:7]=1.S(Cl)(Cl)=O.CO.[C:24]([O-])(O)=O.[Na+]>C1COCC1>[CH3:24][O:16][C:15](=[O:17])[CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68738381HCID 68738381, compound2×

Product 1

HCID 68736834HCID 68736834, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(5-bromo-pyridin-3-yl)-phenyl]-acetic acid (Intermediate 94) (1 eq, 4.1 mmol, 1.2 g) in THF (15 ml) is added thionyl chloride (1.5 eq, 6.16 mmol, 0.45 ml), and the resulting mixture is stirred for 30 min at r.t. Then MeOH (3 eq, 12.3 mmol, 0.5 ml) is added and stirring is continued for another 20 h. Addition of 10% aqueous NaHCO3 solution is followed by extraction with EtOAc. The organic layer is dried with MgSO4, filtered, and the solvents are removed in vacuo. Purification or the crude mixture by column chromatography (hexane/EtOAc) gives the title compound; [M+H]+=306/308.

Workup

  1. stirringstirring
  2. waitis continued for another 20 h
  3. extractionis followed by extraction with EtOAc
  4. dry with materialThe organic layer is dried with MgSO4
  5. filtrationfiltered
  6. customthe solvents are removed in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-51120344e85d42a9aea2848b14f2eab9
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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