Thionyl Chloride → 2-(3-(Chloromethyl)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

HRID 2193716Notes

Reaction equation

HRID 2193716 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[C:16]([CH2:20]O)[CH:17]=[CH:18][CH:19]=3)[S:13][C:6]=12.S(Cl)([Cl:31])=O>>[Cl:31][CH2:20][C:16]1[CH:15]=[C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:2]=3[F:1])[CH:11]=2)[CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 58790269(3-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)methanol

Product 1

HCID 587902112-(3-(Chloromethyl)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridineYield 93%

Procedure

The hydroxy-compound 147 (685 mg, 1.73 mmol) was suspended in thionyl chloride (8.6 mL) and the reaction mixture was refluxed for about one hour. The mixture was cooled to RT then poured into an ice/water mixture. The resultant solid was collected by filtration, washed with water and well dried to afford title compound 148 as a yellow solid (730 mg, 93% yield). MS (m/z): 415.0 (M+H).

Workup

  1. temperaturethe reaction mixture was refluxed for about one hour
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with water
  4. customwell dried

Sources & evidence

ORD record
ord-7c1c9994a959480981a904a27a5fd5e2
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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