Acetic Acid → HCID 73051477, compound

HRID 1048716Notes

Reaction equation

HRID 1048716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][C:11]=2[CH2:19][O:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25]C)=[O:24])=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+].C(O)(=O)C>O.O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][C:11]=2[CH2:19][O:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([OH:25])=[O:24])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 73051807HCID 73051807, compound

Product 1

HCID 73051477HCID 73051477, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.65 g (1.542 mmol) of methyl 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)benzoate were solubilized with magnetic stirring in 30 ml of a mixture consisting of ethanol and of tetrahydrofurane (1/1, v/v) and then 15.42 ml (15.42 mmol) of a 1N NaOH aqueous solution were added. The mixture was stirred at r.t. for 16 h before adding 20 ml of water and then 0.883 ml (15.42 mmol) of acetic acid. The formed precipitate was isolated by filtration, washed with 10 ml of water and dried in a vacuum bell jar in order to obtain 0.518 g (yield=81%) of 2-((3-((4-fluoro-phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)benzoic acid as a pale yellow solid. LC-MS: m/z=387 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 12.72 (s, 1H), 8.64 (d, J=5.5 Hz, 1H), 7.78-7.59 (m, 4H), 7.45 (d, J=6.2 Hz, 2H), 7.41-7.24 (m, 3H), 7.14 (t, J=6.8 Hz, 1H), 7.00 (t, J=7.3 Hz, 1H), 5.42 (s, 2H).

Workup

  1. customThe formed precipitate was isolated by filtration
  2. washwashed with 10 ml of water
  3. customdried in a vacuum bell jar in order

Sources & evidence

ORD record
ord-414024cde7d440af9fe7323afe315be8
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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