Sodium Iodide → 1-(4-chloro-3-fluorobenzyl)-5-(benzo[d]thiazol-2-yl)pyridin-2(1H)-one

HRID 1948197Notes

Reaction equation

C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[Na+].[I-].[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][C:22]=1[F:29]>C(#N)C>[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:8]2[CH:7]=[C:6]([C:9]3[S:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH:5]=[CH:4][C:3]2=[O:2])=[CH:23][C:22]=1[F:29]

Participants

Conditions

Temperature: 90 °C

Procedure

According to Scheme 4, Step 1: A mixture of 2-(6-methoxypyridin-3-yl)benzo[d]thiazole (1 eq, 0.25 mmol, 60 mg), NaI (5 eq, 1.20 mmol, 0.19 g) and 4-chloro-3-fluorobenzylbromide (5 eq, 1.20 mmol, 0.28 g) in acetonitrile (10 mL) was stirred for 14 hours at 90° C. The crude residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 95/5 as eluent to afford 1-(4-chloro-3-fluorobenzyl)-5-(benzo[d]thiazol-2-yl)pyridin-2(1H)-one (0.14 mmol, 0.05 g, 58%) as a beige solid.

Workup

customThe crude residue was partitioned between CH2Cl2 and water
extractionThe aqueous layer was extracted with CH2Cl2
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
customevaporated
customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record: ord-76ff8b448aea4196abc137e7c73da643
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399493B2

Reaction notes

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