Sodium Carbonate → 3-(4-Fluorophenyl)imidazo[1,2-a]pyridine-8-carboxylic acid

HRID 1423033Notes

Reaction equation

HRID 1423033 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[N:7]([C:11](I)=[CH:12][N:13]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:11]2[N:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]3=[N:13][CH:12]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 57355257Methyl 3-iodoimidazo[1,2-a]pyridine-8-carboxylate

Product 1

HCID 671983833-(4-Fluorophenyl)imidazo[1,2-a]pyridine-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To a degassed (with Argon gas) solution of 3-iodo-imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (2.2 g, 7.3 mmol) and 4-fluorophenyl boronic acid (1.48 g, 9.44 mmol) in a 1:1 mixture of ethanol-benzene (100 mL) is added an aqueous solution of 2 M sodium carbonate (9 mL, 18 mmol) and tetrakis(triphenylphosphine) palladium (0) (0.42 g, 0.36 mmol) and the reaction mixture is warmed at reflux. After 16 hours, the reaction mixture is filtered through filter agent washing with EtOAc. The filtrate is diluted with water and the organic layer is separated. The pH of the aqueous layer is adjusted to 4-5 with 6 N aqueous HCl. The solid is collected by filtration and triturated with Et2O to afford the title compound. Mp: >400° C.

Workup

  1. temperaturethe reaction mixture is warmed
  2. temperatureat reflux
  3. filtrationthe reaction mixture is filtered
  4. filtrationthrough filter agent
  5. washwashing with EtOAc
  6. additionThe filtrate is diluted with water
  7. customthe organic layer is separated
  8. filtrationThe solid is collected by filtration
  9. customtriturated with Et2O

Sources & evidence

ORD record
ord-bb360b9d0fb74089a79dbb69971eaf60
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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