Diisopropylethylamine → Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoate

HRID 14301

Reaction equation

HRID 14301 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=N[C:34]2[CH:35]=[CH:36][CH:37]=[N:38][C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NCCC)C>CN(C=O)C>[CH2:33]([N:38]([CH2:37][CH2:36][CH3:35])[C:5]([C:4]1[CH:8]=[C:9]([CH:10]=[C:2]([I:1])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7])[CH3:34]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 883981-Propanamine, N-ethyl-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 21086183Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodo-5-(methoxycarbonyl)benzoic acid (1 g, 3.3 mmol) is dissolved in DMF (10 mL), and diisopropylethylamine (1.7 mL, 9.8 mmol), HATU (1.5 g, 3.9 mmol), and N-ethylpropylamine (572 μL, 4.9 mmol) are added. The reaction stirred at room temperature 16 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40% ethyl acetate/hexane) provides the title compound. ESI MS m/z 376.1 [M+H]+.

Workup

  1. customThe reaction is partitioned between ethyl acetate and water
  2. washThe organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-de38f441747b4cb9bf8eb1004c3289c0
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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