Triphenylphosphine → 5-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

HRID 402394Notes

Reaction equation

HRID 402394 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH2:14][OH:15])=[N:6][CH:7]=1.[CH2:16]([O:18][C:19]([C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][N:22]=1)=[O:20])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:16]([O:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:15][CH2:14][C:9]2[N:10]([CH3:13])[N:11]=[N:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=2)=[CH:23][N:22]=1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23145820Ethyl 5-hydroxypyridine-2-carboxylateHCID 67499388[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanol

Product 1

HCID 674981475-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanol (416 mg, 2.0 mmol), 5-hydroxy-pyridine-2-carboxylic acid ethyl ester (362 mg, 2.60 mmol) and triphenylphosphine (682 mg, 2.6 mmol) in THF (10 mL) was added diethyl azodicarboxylate (40% in toluene, 1.19 mL, 2.6 mmol) dropwise at 0° C. The reaction mixture was then stirred at room temperature for 1 h and then evaporated. Purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) afforded the title compound (386 mg, 77%) as a white solid after recrystallisation from ethyl acetate. MS: m/e=358.3 [M+H]+.

Workup

  1. customevaporated
  2. customPurification by chromatography (silica, 50 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-edb138d09b094225b6c3e2aca3ce82a8
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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