Thionyl Chloride → 2-(2-Chloromethyl-furo[3,2-b]pyridin-6-yloxy)-thiazolo[4,5-b]pyridine

HRID 1947506Notes

Reaction equation

HRID 1947506 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[C:13]2[O:19][C:18]([CH2:20]O)=[CH:17][C:14]2=[N:15][CH:16]=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:20][C:18]1[O:19][C:13]2[C:14](=[N:15][CH:16]=[C:11]([O:10][C:2]3[S:1][C:9]4[C:4]([N:3]=3)=[N:5][CH:6]=[CH:7][CH:8]=4)[CH:12]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride3×HCID 59577380[6-(Thiazolo[4,5-b]pyridin-2-yloxy)-furo[3,2-b]pyridin-2-yl]-methanol

Product 1

HCID 595774422-(2-Chloromethyl-furo[3,2-b]pyridin-6-yloxy)-thiazolo[4,5-b]pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of [6-(thiazolo[4,5-b]pyridin-2-yloxy)-furo[3,2-b]pyridin-2-yl]-methanol (50 mg, 0.17 mmol) in DCM (1.6 mL) was added thionyl chloride (0.020 mL, 0.25 mmol). After 5 min, more thionyl chloride (0.020 mL, 0.25 mmol) was added to the suspension. After 2 h, additional thionyl chloride (0.020 mL, 0.25 mmol) was added. The solution was stirred (rt, 16 h) and concentrated to remove all volatiles to provide the product as a beige solid (53 mg, 99%). MS (ESI): mass calcd. for C14H8ClN3O2S, 317.00; m/z found, 317.9 [M+H]+.

Workup

  1. waitAfter 2 h
  2. concentrationconcentrated
  3. customto remove all volatiles

Sources & evidence

ORD record
ord-28f7e24b34f94c1989714c3090d9b6a1
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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