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PyBOP → 5-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

HRID 423292
Notes
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Reaction equation

HRID 423292 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)=[NH:4].[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:27])[CH3:26])[C:18](O)=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([C:18]2[O:1][N:2]=[C:3]([C:5]3[CH:6]=[C:7]4[C:11](=[CH:12][CH:13]=3)[NH:10][CH:9]=[CH:8]4)[N:4]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:26])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2724699PyBOPHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178513238HCID 178513238, compound

Product 1

HCID 593183535-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazoleYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

D1 (500 mg), D4 (611 mg) and PyBOP (1.66 g) were dissolved in DMF and stirred overnight. The reaction mixture was then evaporated and partitioned between EtOAc and H2O. The organic layer was washed with H2O (×2) then brine, dried over MgSO4, filtered and evaporated to give the crude product. This was purified on a silica cartridge, eluting with a 0 to 50% mixture of Et2O in hexane to give the title compound (120 mg) as a white solid. δH (CDCl3, 400 MHz): 1.43 (6H, d), 4.69 (1H, septet), 6.92 (1H, s), 7.04 (1H, d), 7.25 (1H, s), 7.48 (1H, d), 8.00 (1H, d), 8.07 (1H, d), 8.25 (1H, s), 8.39 (1H, br. s), 8.50 (1H, s). MS (ES): C19H16ClN3O2 requires 353; found 354 (MH+).

Workup

  1. customThe reaction mixture was then evaporated
  2. custompartitioned between EtOAc and H2O
  3. washThe organic layer was washed with H2O (×2)
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customThis was purified on a silica cartridge
  9. washeluting with a 0 to 50% mixture of Et2O in hexane

Sources & evidence

ORD record
ord-4f7805d80bb0444b915b9cd35f8d77b5
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101775B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes