Sodium chlorodifluoroacetate → HCID 86690755, compound

HRID 1471713Notes

Reaction equation

HRID 1471713 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]3[C:13]([CH:19]=[O:20])=[CH:14][C:15](=[O:18])[NH:16][CH:17]=3)[C:5]=12.Cl[C:22]([F:27])([F:26])C([O-])=O.[Na+]>CC#N>[F:26][CH:22]([F:27])[O:18][C:15]1[CH:14]=[C:13]([C:12]([O:11][CH2:10][C:6]2[C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:17][N:16]=1)[CH:19]=[O:20]

Participants

4

Reactant 2

HCID 2734985Sodium chlorodifluoroacetateHCID 71620964HCID 71620964, compound

Product 1

HCID 86690755HCID 86690755, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-oxo-1,2-dihydropyridine-4-carbaldehyde (100 mg, 0.37 mmol, 1 equiv) in CH3CN (10 mL) was added sodium 2-chloro-2,2-difluoroacetate (84.5 mg, 0.56 mmol, 1.5 eq.). The mixture was stirred at rt O/N and concentrated. The crude was purified on silica gel using 10% MeOH/DCM as eluent to give 2-(difluoromethoxy)-5-(imidazo[1,2-a]pyridin-8-ylmethoxy)isonicotinaldehyde (6.0 mg, 5%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.46 (s, 1H), 8.14 (s, 1H), 8.10 (d, J=7.0 Hz, 1H), 7.61 (s, 2H), 7.44 (t, J=60.0 Hz, 1H), 7.24-7.27 (m, 2H), 6.79 (t, J=7.0 Hz, 1H), 5.63 (s, 2H). LRMS (M+H+) m/z 320.0.

Workup

  1. concentrationconcentrated
  2. customThe crude was purified on silica gel using 10% MeOH/DCM as eluent

Sources & evidence

ORD record
ord-e333cdd6c88d40d692220f80251341b9
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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