Oxalyl chloride → (2-[4-(4-Chloro-5-fluoro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenoxy]ethyl)dimehtylamine

HRID 2243593Notes

Reaction equation

HRID 2243593 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:22][C:15]3[N:16]=[CH:17][C:18]([F:21])=[C:19](O)[C:14]=3[C:13]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:8][CH:7]=1.C(Cl)(=O)C([Cl:33])=O>C(Cl)(Cl)Cl>[Cl:33][C:19]1[C:18]([F:21])=[CH:17][N:16]=[C:15]2[O:22][C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:29])[CH3:1])=[CH:7][CH:8]=3)=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]=12

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 178483875HCID 178483875, compound

Product 1

HCID 58608099(2-[4-(4-Chloro-5-fluoro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenoxy]ethyl)dimehtylamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 2-[4-(2-dimethylaminoethoxy)-phenyl]-5-fluoro-3-phenyl-furo[2,3-b]pyridin-4-ol (6) (121.0 mg, 0.31 mmol) and oxalyl chloride (196.0 mg, 1.54 mmol) in chloroform (3.0 mL) was stirred at 60° C. for 1 hr. The solvent was removed, and the residue was purified by preparative HPLC to give the title compound. MS (m/z), M+H+ 411.1.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-40c808bde1a74f65bd90961bef3e5b22
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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