Thionyl Chloride → 2-(2-Chloromethyl-benzo[b]thiophen-6-yloxy)-thiazolo[4,5-b]pyridine

HRID 1947489Notes

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]=[CH:13][C:14]2[CH:18]=[C:17]([CH2:19]O)[S:16][C:15]=2[CH:21]=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:19][C:17]1[S:16][C:15]2[CH:21]=[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]=[CH:13][C:14]=2[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of [6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzo[b]thiophen-2-yl]-methanol (0.13 g, 0.4 mmol) in DCM (5 mL) was added thionyl chloride (30 μL, 49 mg, 0.4 mmol) and the reaction mixture was stirred (0° C., 3 h). The reaction mixture was partitioned between DCM (20 mL) and saturated NaHCO3 (10 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×20 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (0.11 g, 77%). MS (ESI): mass calcd. for C15H9ClN2OS2, 332.0; m/z found, 333.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.07-7.91 (m, 2H), 7.77 (d, J=8.7, 1H), 7.40 (dd, J=8.7, 2.2, 1H), 7.31 (d, J=0.4, 1H), 7.25-7.14 (m, 1H), 4.86 (s, 2H).

Workup

customThe reaction mixture was partitioned between DCM (20 mL) and saturated NaHCO3 (10 mL)
customThe organic layer was separated
extractionthe aqueous layer was extracted with DCM (2×20 mL)
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2e256a6f61354563bbd744a9b66fb98e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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