Isobutanol → Methyl 6-[(3-isobutoxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate

HRID 1373180Notes

Reaction equation

HRID 1373180 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:21][CH:22]([CH3:24])[CH3:23])[CH:20]=1)[C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:44](O)[CH:45]([CH3:47])[CH3:46].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:44]([O:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:21][CH:22]([CH3:24])[CH3:23])[CH:20]=1)[C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)=[O:6])[CH:45]([CH3:47])[CH3:46]

Participants

6

Reactant 4

HCID 6560IsobutanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21074241HCID 21074241, compound

Product 1

HCID 21074242Methyl 6-[(3-isobutoxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-[(3-hydroxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate (0.300 g, 0.91 mM), triphenylphosphine (0.238 g, 0.91 mM), iso-butanol (0.084 ml, 0.91 mM) and THF (8 ml) were combined and diisopropylazodicarboxylate (0.18 ml, 0.91 mM) was added dropwise. The mixture was stirred for 15 mins at ambient temperature. The reaction was concentrated under reduced pressure and the resulting brown oil was purified by column chromatography on Kieselgel 60, eluting with a gradient of 50–100% methylene chloride in iso-hexane and then 20% ethyl acetate in methylene chloride to give methyl 6-[(3-isobutoxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate as a colourless solid (0.232 g); [M+H]+ 387; [M−H]− 385.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe resulting brown oil was purified by column chromatography on Kieselgel 60
  3. washeluting with a gradient of 50–100% methylene chloride in iso-hexane

Sources & evidence

ORD record
ord-f95804045a52464581f7cf988a5ca776
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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