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1-(Bromomethyl)-4-chlorobenzene → 5-[1-(4-Chlorobenzyl)-5-methyl-1H-pyrazol-3-yl]-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

HRID 2400590
Notes
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Reaction equation

HRID 2400590 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:8]=2)[CH:3]=1.Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.CC(C)([O-])C.[K+]>C1COCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:6]2[C:2]([CH3:1])=[CH:3][C:4]([C:7]3[O:11][N:10]=[C:9]([C:12]4[CH:13]=[CH:14][C:15]([O:18][C:19]([F:20])([F:22])[F:21])=[CH:16][CH:17]=4)[N:8]=3)=[N:5]2)=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 23665647Potassium tert-butoxideHCID 469016545-(5-methyl-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole2×

Product 1

HCID 462157425-[1-(4-Chlorobenzyl)-5-methyl-1H-pyrazol-3-yl]-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mechanically stirred solution of 5-(5-methyl-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)-phenyl]-1,2,4-oxadiazole (Intermediate C, 60 mg, 0.193 mmol) and 1-(bromomethyl)-4-chlorobenzene (53 mg, 0.215 mmol) in dry THF (2 mL) was added potassium tert-butoxide (24 mg, 0.213 mmol) at a temperature of 0° C. The cooling bath was removed, and the reaction mixture was stirred at rt over night. After the addition of DMF (1 mL), the complete reaction mixture was subjected to preparative HPLC affording the title compound in pure form (68 mg, 81%): 1H NMR (400 MHz, CDCl3) 8.25 (d, 2H), 7.33 (d, 2H), 7.31 (d, 2H), 7.11 (d, 2H), 6.82 (s, 1H), 5.42 (s, 2H), 2.27 (s, 3H); ES-MS m/z 435, HPLC RT (Method K) 1.63 min.

Workup

  1. customThe cooling bath was removed
  2. additionAfter the addition of DMF (1 mL)

Sources & evidence

ORD record
ord-d19e25ab33314c18b24007f39fb4896e
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08796253B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes