4-Hydroxymethylpyridine → HCID 66811834, compound

HRID 1097266Notes

Reaction equation

HRID 1097266 reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[F:19][C:20]1[CH:21]=[C:22]2[CH:28]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[NH:26][C:23]2=[N:24][CH:25]=1.[N:34]1[CH:39]=[CH:38][C:37]([CH2:40]O)=[CH:36][CH:35]=1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[N:34]1[CH:39]=[CH:38][C:37]([CH2:40][N:26]2[C:23]3=[N:24][CH:25]=[C:20]([F:19])[CH:21]=[C:22]3[CH:28]=[C:27]2[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57345886Ethyl 5-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 66811834HCID 66811834, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

9.18 g (36.02 mmol) of 1,1′-(azodicarbonyl)dipiperidine are added, in a quarter of an hour, to a solution, stirred at 20° C., of 5 g (24.02 mmol) of ethyl 5-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (Example 21.3), 3.97 g (36.02 mmol) of (pyridin-4-yl)methanol and 7.5 g (36.02 mmol) of tributylphosphine in 150 ml of toluene. The reaction mixture is stirred at 20° C. for 16 hours, filtered over a celite buffer, concentrated under reduced pressure and then taken up in 100 ml of dichloromethane. The organic solution is washed twice with 50 ml of a 5% aqueous solution of potassium carbonate and then once with 50 ml of water, dried over sodium sulphate and concentrated under reduced pressure. The product obtained is chromatographed on a silica column, elution being carried out with a mixture of heptane and ethyl acetate. 4.5 g of the expected ester are thus isolated.

Workup

  1. filtrationfiltered over a celite buffer,
  2. concentrationconcentrated under reduced pressure
  3. washThe organic solution is washed twice with 50 ml of a 5% aqueous solution of potassium carbonate
  4. dry with materialonce with 50 ml of water, dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe product obtained
  7. customis chromatographed on a silica column, elution
  8. additionbeing carried out with a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-cc12a2fc6cf8491bb81d9f4f2b37f4b8
Source dataset
uspto-grants-2012_03
Patent number
US08143248B2

Reaction notes

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