Lithium Hydroxide → HCID 66986231, compound

HRID 1254065Notes

Reaction equation

HRID 1254065 reaction equation
[I:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=1.[OH-].[Li+]>C(#N)C.O>[I:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66986124HCID 66986124, compound2×

Product 1

HCID 66986231HCID 66986231, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 4-(5-iodo-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl)benzoate (Intermediate 7, Step 3, 1.5 g, 3.58 mmol) and lithium hydroxide (0.257 g, 10.73 mmol) in acetonitrile (6 mL) and water (6 mL) was heated to 50° C. for 2 h. The mixture was concentrated and extracted with EtOAc. The organics were dried (MgSO4) and concentrated to afford 4-(5-iodo-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl)benzoic acid. LCMS: m/z 406.0 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EtOAc
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c5f70c4643634185b25feb5640cc8217
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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