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Acetic Acid → 5-(3-Bromo-5-morpholinomethyl-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]-oxadiazole

HRID 2114942
Notes
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Reaction equation

HRID 2114942 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([CH:7]=O)[O:4][C:3]=1[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:10]=1.C([BH3-])#N.[Na+].C(O)(=O)C.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CO>[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[O:4][C:3]=1[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 221478875-(3-Bromo-5-formyl-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]-oxadiazole

Product 1

HCID 221478365-(3-Bromo-5-morpholinomethyl-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]-oxadiazoleYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 5-(3-bromo-5-formyl-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]-oxadiazole (60 mg, 0.170 mmol), sodium cyanoborohydride (10.5 mg, 0.167 mmol), acetic acid (10.0 μL, 0.173 mmol), and methanol (2.0 mL) under argon was added morpholine (50 μL, 0.57 mmol). The solution was stirred for 24 h and concentrated to dryness. The product was purified by column chromatography (2:1, hexane:ethyl acetate) to yield 12 mg (17%) of 5-(3-bromo-5-morpholinomethyl-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]-oxadiazole as a white solid. 1H NMR (CDCl3): 8.12 (d, J=8.51 Hz, 2H), 7.49 (d, J=8.52 Hz, 2H), 6.60 (s, 1H), 3.74 (t, J=4.67 Hz, 4H), 3.67 (s, 2H), 2.56 (t, J=4.67 Hz, 4H); and to also yield 12 mg (20%) of 5-(3-bromo-5-hydroxymethyl-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]-oxadiazole as a white solid. 1H NMR (CDCl3): 8.11 (dd, J=8.79, 2.20 Hz, 2H), 7.49 (dd, J=8.79, 2.20 Hz, 2H), 6.67 (s, 1H), 4.77 (d, J=6.32 Hz, 2H), 2.09 (t, J=6.46 Hz, 4H).

Workup

  1. concentrationconcentrated to dryness
  2. customThe product was purified by column chromatography (2:1, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-74514d1a40f64f0caadab5dc82b4f805
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07435750B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes