Thionyl Chloride → 2-[4-(Chloromethyl)phenoxy][1,3]thiazolo[5,4-b]pyridine

HRID 547346Notes

Reaction equation

HRID 547346 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[S:3][C:2]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=1.O=S(Cl)[Cl:21]>C(Cl)Cl>[Cl:21][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:2]2[S:3][C:4]3[C:9]([N:1]=2)=[CH:8][CH:7]=[CH:6][N:5]=3)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57448386[4-([1,3]Thiazolo[5,4-b]pyridin-2-yloxy)phenyl]methanol

Product 1

HCID 574483872-[4-(Chloromethyl)phenoxy][1,3]thiazolo[5,4-b]pyridineYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-([1,3]thiazolo[5,4-b]pyridin-2-yloxy)phenyl]methanol (140 mg, 0.542 mmol) in CH2Cl2 (3.6 mL) was added SOCl2 (43 μL, 0.596 mmol, 1.1 equiv.). The solution was allowed to stir under N2 at rt for 4 h. The reaction mixture was then concentrated to afford the desired product as a cream-colored solid (157 mg, 92%). MS (ESI): mass calcd. for C13H9ClN2OS, 276.0; m/z found, 277.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 8.47 (dd, J=4.4, 1.5, 1H), 8.11 (dd, J=8.2, 1.5, 1H), 7.65-7.57 (m, 2H), 7.56-7.47 (m, 3H), 4.85 (s, 2H).

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-4bcad95c9f03437c82dbd8423b08e74d
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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