Cesium carbonate → 1-(6-Bromobenzo[d]thiazol-2-yl)azetidin-3-ol

HRID 1691972Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1)=[S:11].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]=[C:10]([N:12]3[CH2:15][CH:14]([OH:16])[CH2:13]3)[S:11][C:2]=2[CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

N-(2,4-Dibromophenyl)-3-hydroxyazetidine-1-carbothioamide (0.366 g, 1.0 mmol) and Cs2CO3 (0.489 g, 1.5 mmol) were suspended in acetonitrile (10 mL), and the stirred reaction mixture was heated under microwave irradiation at 150° C. for 12 minutes. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (2:1 to 1:2 hexane/ethyl acetate) to provide 1-(6-bromobenzo[d]thiazol-2-yl)azetidin-3-ol. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.85-3.91 (m, 2H), 4.29-4.36 (m, 2H), 4.61-4.72 (m, 1H), 5.90 (d, J=8 Hz, 1H), 7.36-7.44 (m, 2H), 8.02-8.03 (m, 1H); MS (DCI/NH3) m/z 285 (M+H)+.

Workup

customthe stirred reaction mixture
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel chromatography (2:1 to 1:2 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-917224ee00b04dbb80b7d0afc8694c28
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153813B2

Reaction notes

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