Methanol → HCID 73052926, compound

HRID 1048689Notes

Reaction equation

HRID 1048689 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][O:19][CH2:20][C:21]([O:23]CC)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+:29]>O1CCCC1>[C:1]1([C:7]#[C:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][O:19][CH2:20][C:21]([O-:23])=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[Na+:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 73051638HCID 73051638, compound

Product 1

HCID 73052926HCID 73052926, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.061 g (0.182 mmol) of ethyl 2-((3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)acetate were solubilised with magnetic stirring in 3 ml of a mixture consisting of methanol and tetrahydrofurane (1/1, v/v) and then 0.173 ml (0.173 mmol) of a 1N NaOH aqueous solution were added. The mixture was stirred at r.t. for 2 d before being concentrated in vacuo. The crude residue was triturated in 3 ml of diisopropyl ether, the obtained solid was isolated by filtration and dried under a vacuum bell jar in order to obtain 0.027 g (yield=45%) of sodium 2-((3-(phenyl ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)acetate. LC-MS: m/z=307 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.62 (d, J=6.7 Hz, 1H), 7.79-7.58 (m, 3H), 7.45 (dd, J=8.8, 7.2 Hz, 4H), 7.13 (t, J=6.5 Hz, 1H), 4.74 (s, 2H), 3.70 (s, 2H)

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe crude residue was triturated in 3 ml of diisopropyl ether
  3. customthe obtained solid was isolated by filtration
  4. customdried under a vacuum bell jar in order

Sources & evidence

ORD record
ord-77e4738ebc704fa5afd830abe36dbda6
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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