Dimethylformamide → 2-(4-Isopropylpiperazin-1-yl)benzothiazole-5-carbaldehyde

HRID 1619263Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([N:10]3[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:19]=1.[Li]CCCC.CN([CH:28]=[O:29])C>C1COCC1>[CH:16]([N:13]1[CH2:14][CH2:15][N:10]([C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([CH:28]=[O:29])=[CH:19][C:6]=3[N:7]=2)[CH2:11][CH2:12]1)([CH3:18])[CH3:17]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 5-bromo-2-(4-isopropylpiperazin-1-yl)benzothiazole (300 mg, 0.88 mmol) in dry THF was added n-BuLi dropwise over 10 min at −78° C. After 30 min, DMF was added dropwise at −78° C. The reaction mixture was then stirred for 1.5 h at −78° C., quenched with water and extracted with ethyl acetate to give a residue which was purified by column chromatography on silica gel (eluent: 1% dichloromethane in methanol). This afforded 240 mg (94%) of 2-(4-isopropylpiperazin-1-yl)benzothiazole-5-carbaldehyde.

Workup

customquenched with water
extractionextracted with ethyl acetate
customto give a residue which
customwas purified by column chromatography on silica gel (eluent: 1% dichloromethane in methanol)

Sources & evidence

ORD record: ord-d3307fe50613436394003ad666821736
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772285B2

Reaction notes

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