Bromotrichloromethane → Methyl {2-{4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-1,3-oxazol-4-yl}carboxylate

HRID 1716823Notes

Reaction equation

[N:1]1([CH2:10][C:11]2[CH:26]=[CH:25][C:14]([C:15]([NH:17][C@H:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:19][OH:20])=O)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.BrC(Cl)(Cl)Cl.C1CCN2C(=NCCC2)CC1>C1COCC1.C(Cl)Cl>[N:1]1([CH2:10][C:11]2[CH:26]=[CH:25][C:14]([C:15]3[O:20][CH:19]=[C:18]([C:21]([O:23][CH3:24])=[O:22])[N:17]=3)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred solution of methyl N-{4-[(1H-benzimidazol-1-yl)methyl]benzoyl}-serinate (2.8 g, 7.93 mmol) in THF is treated with Burgess Reagent (2.26 g, 9.45 mmol) and activated 4 Å molecular sieves (1 g), stirred at 60° C. for 2 h, cooled to room temperature and concentrated under reduced pressure. A solution of the resultant residue (0.1 g, 0.29 mmol) in CH2Cl2 is cooled to 0° C., treated with bromo trichloromethane (0.06 g, 0.33 mmol) and DBU (0.05 g, 0.33 mmol), stirred at room temperature overnight and concentrated under reduced pressure. The resultant residue is purified by column chromatography (silica, CH3OH/CHCl3 0→5%) to give the title product in 52% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 8.28 (s, 1H); 8.08 (d, J=8 Hz, 2H); 8.00 (m, 1H); 7.85 (d, J=8 Hz, 2H); 7.30 (m, 5H); 5.43 (s, 2H); 3.95 (s, 3H). LCMS (ESI+) 334 (MH+).

Workup

temperaturecooled to room temperature
concentrationconcentrated under reduced pressure
stirringstirred at room temperature overnight
concentrationconcentrated under reduced pressure
customThe resultant residue is purified by column chromatography (silica, CH3OH/CHCl3 0→5%)

Sources & evidence

ORD record: ord-b66fb8fcd3a141fca1f234ca61375897
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803825B2

Reaction notes

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