HCID 178470049, compound → Ethyl 2-(5-bromobenzo[D]thiazol-2-YL)acetate

HRID 424941

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:9]=2[NH:10][C:11]=1O)=[O:5])[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:11]1[S:7][C:8]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:9]=2[N:10]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of the crude material from Example 2C (2.7 g, 8.5 mmol) in acetic acid (60 mL) and heated to 110° C. Then Zn (18 equivalents) was added slowly in portions over 30 min to the mixture under nitrogen. After the completion the mixture was cooled to room temperature and the Zn residue was filtered off. The filter cake was washed with MeOH. And the combined filtrate was stripped to dryness. The residue was dissolved in 70 mL of chloroform and washed with water twice. The chloroform solution was dried with anhydrous MgSO4 and concentrated to dryness. The crude product was purified by column chromatography (silica gel, 10% EtOAc/Hexane). Purified yield for the three steps from example 2B-2D was 1.11 g (43.3%).

Workup

temperatureAfter the completion the mixture was cooled to room temperature
filtrationthe Zn residue was filtered off
washThe filter cake was washed with MeOH
dissolutionThe residue was dissolved in 70 mL of chloroform
washwashed with water twice
dry with materialThe chloroform solution was dried with anhydrous MgSO4
concentrationconcentrated to dryness
customThe crude product was purified by column chromatography (silica gel, 10% EtOAc/Hexane)
customPurified
customyield for the three steps from example 2B-2D

Sources & evidence

ORD record: ord-0c77c925ecbb4075b1c0c6b60347fb41
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106088B2

Linked notes

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