Triethylamine → HCID 68233567, compound

HRID 1429396Notes

Reaction equation

HRID 1429396 reaction equation
C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:27]1([CH2:33][CH:34]([OH:38])[CH2:35][CH:36]=[CH2:37])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.I[C:40]1[CH:49]=[CH:48][CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(=O)OCC>[OH:38][CH:34]([CH2:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:35]/[CH:36]=[CH:37]/[C:40]1[CH:49]=[CH:48][CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43]

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 11776TriphenylphosphineHCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 11829757HCID 11829757, compound

Product 1

HCID 68233567HCID 68233567, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of triethylamine (7.6 mL, 54.7 mmol), triphenylphosphine (0.778 g, 2.97 mmol) and palladium acetate (0.35 g, 1.56 mmol) in 1,4-dioxane (50 mL) was refluxed to form a homogeneous dark-red solution. The reaction temperature was then reduced to just below reflux. Compound 30b (4.56 g, 28 mmol), methyl 2-iodobenzoate (4.10 g, 15.6 mmol) and triethylamine (2.88 mL, 10.2 mmol) were added subsequently with stirring. The reaction mixture was then refluxed for about 30 min until TLC showed the SM had disappeared. The reaction mixture was filtered hot through celite, which was washed with 1,4-dioxane. The combined filtrate and washings were evaporated in vacuo to a small volume and purified by CC using PE:EA=5:1 as mobile phase to give the desired product (2.59 g, 56% yield).

Workup

  1. temperaturewas refluxed
  2. customto form a homogeneous dark-red solution
  3. temperaturebelow reflux
  4. temperatureThe reaction mixture was then refluxed for about 30 min until TLC
  5. filtrationThe reaction mixture was filtered hot through celite, which
  6. washwas washed with 1,4-dioxane
  7. customThe combined filtrate and washings were evaporated in vacuo to a small volume
  8. custompurified by CC

Sources & evidence

ORD record
ord-a279519a91b54d2999eab69e79eecaec
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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