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Carbon tetrabromide → ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257423
Notes
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Reaction equation

HRID 1257423 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]([OH:14])=O)[CH:10]=1)=[O:5])[CH3:2].Cl.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([NH:23][NH2:24])=O.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:16][C:17]([F:28])([F:29])[C:18]1[CH:19]=[C:20]([C:21]2[O:14][C:12]([CH2:11][N:9]3[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]3)=[N:24][N:23]=2)[CH:25]=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59557975[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]acetic acidHCID 669395863-(Trifluoromethyl)benzohydrazide hydrochloride

Product 1

HCID 58127966ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}methyl)-1H-pyrazole-4-carboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound (1.0 g) obtained in Example 115b in dichloromethane (15 ml) was cooled in an ice bath, N,N′-carbonyldiimidazole (0.81 g) was added and the mixture was stirred for 30 min. 3-(Trifluoromethyl)benzohydrazide hydrochloride (1.2 g) was added, and the mixture was stirred at the same temperature for 45 min. Then, carbon tetrabromide (3.32 g) and triphenylphosphine (2.6 g) were added, and the mixture was further stirred at the same temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate) to give the title compound (0.64 g) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 45 min
  2. stirringthe mixture was further stirred at the same temperature for 2 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate)

Sources & evidence

ORD record
ord-85aff709d24a4076868f36e0b13b050f
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461348B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes