3-Chloro-2-fluorophenylboronic Acid → HCID 71255708, compound

HRID 1508325Notes

Reaction equation

HRID 1508325 reaction equation
[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:20][C:21]1[N:22]=[CH:23][NH:24][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].ClC1C(F)=C(B(O)O)C=CC=1>CO.C(Cl)Cl>[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:24]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([CH3:20])[N:22]=[CH:23]2)[CH:5]=[CH:6][CH:7]=1.[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 162171583-Chloro-2-fluorophenylboronic AcidHCID 71255671HCID 71255671, compoundHCID 178470400HCID 178470400, compound

Product 2

HCID 71255671HCID 71255671, compoundYield 1%HCID 71255708HCID 71255708, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 1-(3-chloro-2-fluorophenyl)-5-methyl-1H-imidazole-4-carboxylate: Using a modified procedure of Sreedhar. (Reference: Sreedhar, B., Synthesis, 795 (2008)). To a suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (0.530 g, 3.44 mmol) and (3-chloro-2-fluorophenyl)boronic acid (0.500 g, 2.87 mmol) in MeOH (5.74 mL) was added cuprous oxide (0.041 g, 0.287 mmol). The resulting purple suspension was stirred vigorously under an atmosphere of air (drying tube used). After 20 h, the reaction mixture was filtered to remove the solids and the clear blue filtrate was concentrated to give a blue solid. The blue solid was suspended in DCM and filtered to remove the solids and the blue filtrate was concentrated to give a pale blue solid weighing 0.187 g. Purification by normal phase chromatography gave ethyl 1-(3-chloro-2-fluorophenyl)-4-methyl-1H-imidazole-5-carboxylate (0.0187 g, 2%) as a clear, colorless residue and ethyl 1-(3-chloro-2-fluorophenyl)-5-methyl-1H-imidazole-4-carboxylate (Intermediate 24A) (0.0079 g, 1%) as a clear, colorless residue. MS(ESI) m/z: 283.1 (M+H)+.

Workup

  1. custom(Reference: Sreedhar, B., Synthesis, 795 (2008))
  2. filtrationthe reaction mixture was filtered
  3. customto remove the solids
  4. concentrationthe clear blue filtrate was concentrated
  5. customto give a blue solid
  6. filtrationfiltered
  7. customto remove the solids
  8. concentrationthe blue filtrate was concentrated
  9. customto give a pale blue solid
  10. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-243773a79cda45c69b6e2686b61a6c9d
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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