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

HRID 1716823
Notes
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Reaction equation

HRID 1716823 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 68666178HCID 68666178, compound

Product 1

HCID 57550219Methyl {2-{4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-1,3-oxazol-4-yl}carboxylateYield 52%

Reagents, catalysts & solvents

2
HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

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

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. stirringstirred at room temperature overnight
  4. concentrationconcentrated under reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes