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Ethyl 4-(bromomethyl)picolinate → HCID 59508608, compound

HRID 1095930
Notes
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Reaction equation

HRID 1095930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:23])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([OH:21])([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=1)[C:10]([F:13])([F:12])[F:11].[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[C:33]([CH2:35]Br)[CH:32]=[CH:31][N:30]=1)=[O:28])[CH3:25]>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[C:33]([CH2:35][O:23][C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:22])[C:9]([OH:21])([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=3)[C:10]([F:13])([F:11])[F:12])=[C:2]([Cl:1])[CH:3]=2)[CH:32]=[CH:31][N:30]=1)=[O:28])[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 21781508Ethyl 4-(bromomethyl)picolinateHCID 252541463-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol

Product 1

HCID 59508608HCID 59508608, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol (100 mg, obtained in Example 93, step 6) and ethyl-4-(bromomethyl)-pyridine-2-carboxylate (85 mg, [CAS Reg. No. 153994-03-7]) were dissolved in DMF (5 mL) followed by addition of silver carbonate (80 mg). The mixture was heated to 80° C. for 3 hours. The reaction mixture was cooled, poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a yellow foam (98 mg, 63%). MS (m/e)=509.3 [MH+].

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted two times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-54837cd5ac4f459284d38e8ceecb1617
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138189B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes