Isopropanol → 6-(4-(Benzyloxy)-6-chlorobenzofuran-2-yl)-2-bromoimidazo[2,1-b][1,3,4]thiadiazole

HRID 625124Notes

Reaction equation

HRID 625124 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[CH:15]=[C:16]([C:18](=O)[CH2:19]Br)[O:17][C:13]=2[CH:12]=[C:11]([Cl:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:23][C:24]1[S:28][C:27]([NH2:29])=[N:26][N:25]=1.CC(O)C>>[CH2:1]([O:8][C:9]1[C:14]2[CH:15]=[C:16]([C:18]3[N:29]=[C:27]4[N:26]([CH:19]=3)[N:25]=[C:24]([Br:23])[S:28]4)[O:17][C:13]=2[CH:12]=[C:11]([Cl:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 36508832-Amino-5-bromo-1,3,4-thiadiazoleHCID 86700910HCID 86700910, compound

Product 1

HCID 867009096-(4-(Benzyloxy)-6-chlorobenzofuran-2-yl)-2-bromoimidazo[2,1-b][1,3,4]thiadiazoleYield 73.6%

Conditions

Temperature
80 °C

Procedure

A sealable vessel was charged with 1-(4-(benzyloxy)-6-chlorobenzofuran-2-yl)-2-bromoethanone (Example 37F, 1.48 g, 3.51 mmol), 5-bromo-1,3,4-thiadiazol-2-amine (0.632 g, 3.51 mmol) and IPA (25 mL, 324 mmol). The reaction mixture was heated in an oil bath at 80° C. for 6 hours then heated in the microwave at 150° C. for 1 hour. The reaction mixture was allowed to stand for 1 hour and the insoluble material was filtered off and rinsed with MeOH to give the desired product as a brown solid (1.19 g, 2.58 mmol, 73.6% yield). LC (Method A): 2.549 min. LCMS (APCI) calcd for C19H12BrClN3O2S [M+H]+ m/z 459.95, found 460.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 8.74 (s, 1H), 7.55-7.50 (m, 2H), 7.45-7.34 (m, 4H), 7.17 (d, J=0.8 Hz, 1H), 7.02 (d, J=1.6 Hz, 1H), 5.32 (s, 2H).

Workup

  1. temperaturethen heated in the microwave at 150° C. for 1 hour
  2. filtrationthe insoluble material was filtered off
  3. washrinsed with MeOH

Sources & evidence

ORD record
ord-f1ab29dcd21941f3a73910a295d0c635
Source dataset
uspto-grants-2016_04
Patent number
US09303065B2

Reaction notes

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