Thionyl Chloride → HCID 121386210, compound

HRID 2202911Notes

Reaction equation

HRID 2202911 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:18]([C:20]([CH3:25])=[C:21]([CH2:23]O)[N:22]=4)[CH:19]=3)[C:10](=[O:26])[CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:31])=O>C(Cl)Cl>[Cl:31][CH2:23][C:21]1[N:22]=[C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:27]=[CH:28][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][C:10]3=[O:26])=[CH:19][N:18]2[C:20]=1[CH3:25]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89691111HCID 89691111, compound

Product 1

HCID 121386210HCID 121386210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-((4-fluorobenzyl)oxy)-1-(2-(hydroxymethyl)-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (120 mg) in DCM (1 ml) was added thionyl chloride (1 ml), and the mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo, diluted with DCM and quenched with aqueous NaHCO3 under ice-cold condition. The organic layer was separated, washed successively with water and brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (120 mg) as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with DCM
  3. customquenched with aqueous NaHCO3 under ice-cold condition
  4. customThe organic layer was separated
  5. washwashed successively with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46047414d58746c59f719700a91d803f
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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