Water → HCID 178458438, compound

HRID 2236550Notes

Reaction equation

HRID 2236550 reaction equation
[N:1]([CH2:4][C:5]1[N:10]=[C:9]([O:11]CC2C=CC=CC=2)[C:8]([O:19][CH2:20][CH2:21][CH3:22])=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1[N:10]=[C:9]([OH:11])[C:8]([O:19][CH2:20][CH2:21][CH3:22])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 59299959HCID 59299959, compound

Product 1

HCID 178458438HCID 178458438, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-azidomethyl-2-benzyloxy-3-propoxy-pyridine (544 mg, 2.00 mmole), 12 mL of tetrahydrofuran, and triphenylphosphine (524 mg, 2.00 mmole) then water (540 □L, 30.0 mmole) is added and this is stirred at ambient temperature overnight. The reaction mixture is evaporated to dryness in vacuo and then washed with 2:1 hexanes/ethyl acetate and filtered. This resulting solid is taken up in ethanol and hydrogenated over 10% palladium on carbon at 1 atmosphere. The reaction mixture is filtered washed with ethanol, evaporated to give a brownish green solid, 93 mg, (25%), MS (ES+): m/z 183.3 (M+H). This is used as is for the next step.

Workup

  1. customThe reaction mixture is evaporated to dryness in vacuo
  2. washwashed with 2:1 hexanes/ethyl acetate
  3. filtrationfiltered
  4. filtrationThe reaction mixture is filtered
  5. washwashed with ethanol
  6. customevaporated
  7. customto give a brownish green solid, 93 mg, (25%), MS (ES+)

Sources & evidence

ORD record
ord-fd8008e08e4a435fa5fd1e569ff0534a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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