4-Hydroxymethylpyridine → HCID 66811834, compound

HRID 2063290Notes

Reaction equation

HRID 2063290 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-9c1051a5b1794c9eb46a9fc759bfce8f
Source dataset
uspto-grants-2012_10
Patent number
US08288376B2

Reaction notes

Loading…