4-Hydroxymethylpyridine → HCID 66811834, compound

HRID 1666289Notes

Reaction equation

HRID 1666289 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7]O)=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:28][C:29]1[CH:30]=[C:31]2[CH:37]=[C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[NH:35][C:32]2=[N:33][CH:34]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:28][C:29]1[CH:30]=[C:31]2[CH:37]=[C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:35]([CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[C:32]2=[N:33][CH:34]=1

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57345886Ethyl 5-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 66811834HCID 66811834, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.19 g (1.8 mmol) of 4-pyridylmethanol and then 0.48 g (1.8 mmol) of triphenylphosphine are successively added with stirring to a solution of 0.25 g (1.2 mmol) of ethyl 5-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, obtained according to the protocol described in step 1.3, in 10 mL of dry tetrahydrofuran maintained under an inert atmosphere. 0.32 g (1.8 mmol) of diethyl azodicarboxylate is then added dropwise at 0° C. The reaction mixture is then stirred for 72 hours at room temperature and then concentrated under reduced pressure. The resulting oil is purified by chromatography on a column of silica gel, eluting with a mixture of heptane and ethyl acetate. 0.26 g of the expected product is isolated.

Workup

  1. customobtained
  2. temperaturemaintained under an inert atmosphere
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting oil is purified by chromatography on a column of silica gel
  5. washeluting with a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-0ef4689489d140c3ade57961ac370483
Source dataset
uspto-grants-2011_10
Patent number
US08044066B2

Reaction notes

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