(4-Chloro-2-fluoro-5-methoxyphenyl)boronic acid → 2-(4-Chloro-2-fluoro-5-methoxyphenyl)imidazo[1,2-a]pyridine

HRID 1378957Notes

Reaction equation

HRID 1378957 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[CH:10]=1.[Cl:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15](B(O)O)=[C:14]([F:23])[CH:13]=1>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][N:5]3[CH:10]=2)=[C:14]([F:23])[CH:13]=1

Participants

5

Reactant 2

HCID 10932600(4-Chloro-2-fluoro-5-methoxyphenyl)boronic acidHCID 124289572-Bromoimidazo[1,2-a]pyridine

Product 1

HCID 226256052-(4-Chloro-2-fluoro-5-methoxyphenyl)imidazo[1,2-a]pyridineYield 61.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 0.8 g (4.1 mmol) of 2-bromoimidazo[1,2-a]pyridine, 0.8 g (4.2 mmol) of 4-chloro-2-fluoro-5-methoxyphenylboronic acid, and 0.2 g (0.28 mmol) of bis(triphenylphosphine)palladium(II) chloride were heated in 30 ml of glyme at reflux for 2 h. The reaction mixture was partitioned between 250 ml of ethyl acetate and 100 ml of water and the separated organic layer washed with brine and dried over magnesium sulfate. On evaporating in vacuo, the remaining residue was flash chromatographed on silice gel (1:1 hexane/ethyl acetate) to afford 0.7 g of the title compound (m.p. 139°-141° C.). NMR (CDCl3, 400 MHz): δ4.03 (s, 3H), 6.81 (t, 1H), 7.21 (m, 2H), 8.63 (d, 1H), 7.92 (d, 1H), 8.04 (s, 1H), 8.14 (d, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. customThe reaction mixture was partitioned between 250 ml of ethyl acetate and 100 ml of water
  3. washthe separated organic layer washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customOn evaporating in vacuo
  6. customchromatographed on silice gel (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-04a5fd10faa4481f8b2c97238f66e488
Source dataset
uspto-grants-1997_09
Patent number
US05670455

Reaction notes

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