4-Isobutylbenzoic acid → 2-Chloro-5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridine

HRID 2242221Notes

Reaction equation

HRID 2242221 reaction equation
[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:56][C:57]1[N:62]=[CH:61][C:60]([C:63](=[N:65]O)[NH2:64])=[CH:59][CH:58]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>ClCCl>[Cl:56][C:57]1[CH:58]=[CH:59][C:60]([C:63]2[N:65]=[C:9]([C:8]3[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])=[CH:13][CH:12]=3)[O:11][N:64]=2)=[CH:61][N:62]=1

Participants

7

Reactant 5

HCID 381114-Isobutylbenzoic acidHCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 2724699PyBOPHCID 336784996-Chloro-N-hydroxy-nicotinamidine

Product 1

HCID 592042672-Chloro-5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-isobutylbenzoic acid (19.5 g, 110 mmol), PyBOP (57.6 g, 111 mmol), diisopropylethyl amine (19 mL, 111 mmol) and dichloromethane (1.0 L) was stirred at room temperature for 15 minutes and 6-chloro-N′-hydroxypyridine-3-carboximidamide (19.0 g, 111 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours and filtered. The white solid (35.0 g) was treated with TBAF (1M in THF, 159 mL, 158 mmol) and stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, taken up in H2O (1.0 L) and filtered to provide the title compound (29.6 g, 87% yield) as a white solid.

Workup

  1. filtrationfiltered
  2. stirringstirred at room temperature for 12 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-313194ac108c4ac5bf5a2301e949f2b8
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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