6-Methyl-2-pyridinecarboxaldehyde → HCID 59751456, compound

HRID 748647Notes

Reaction equation

HRID 748647 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[CH3:30][C:31]1[N:36]=[C:35]([CH:37]=[O:38])[CH:34]=[CH:33][CH:32]=1>ClCCl>[CH3:30][C:31]1[N:36]=[C:35]([CH:37]([C:2]2[N:3]=[CH:4][N:5]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:6]=2)[OH:38])[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 707376-Methyl-2-pyridinecarboxaldehyde2×HCID 6182524-Iodo-1-tritylimidazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 59751456HCID 59751456, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-iodo-1-tritylimidazole (commercially available) (5.0 g, 11.5 mmol) in dichloromethane (50 mL) at −10° C. was treated with ethyl magnesium bromide (3.8 mL, 11.5 mmol, 3M in ether) and allowed to react for 90 m. A solution of 6-methyl-pyridine-2-carbaldehyde (Intermediate D1) (commercially available from Aldrich) (0.93 g, 7.7 mmol) in dichloromethane (10 mL) was added via syringe at −10° C. and stirred for 45 m. The mixture was quenched with water (50 mL) and with a saturated solution of ammonium chloride (60 mL). The residue was isolated in an aqueous workup, extracting with CHCl3 and purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to give (6-Methyl-pyridin-2-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate D2) as a solid, 3.3 g (˜99%).

Workup

  1. customto react for 90 m
  2. customThe mixture was quenched with water (50 mL) and with a saturated solution of ammonium chloride (60 mL)
  3. customThe residue was isolated in an aqueous workup
  4. extractionextracting with CHCl3
  5. custompurified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-7f7d5fcca4624e7abbe204bc4438d543
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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