Triphenylphosphine → 5-Bromo-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester

HRID 1929912Notes

Reaction equation

HRID 1929912 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([Br:12])[C:9](=[O:13])[NH:8][C:7]=1[C:14]([F:17])([F:16])[F:15])=[O:5])[CH3:2].O[CH2:19][CH:20]1[CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[C:10]([Br:12])[C:9]([O:13][CH2:19][CH:20]2[CH2:22][CH2:21]2)=[N:8][C:7]=1[C:14]([F:17])([F:15])[F:16])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57900861Ethyl 5-bromo-6-hydroxy-2-(trifluoromethyl)nicotinate

Product 1

HCID 675049975-Bromo-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-1,6-dihydro-6-oxo-2-(trifluoromethyl)-3-pyridinecarboxylic acid ethyl ester (CAN 862111-61-3) (1.3 g, 3.6 mmol) was dissolved in THF (15 mL). To the solution were added hydroxymethylcyclopropane (0.35 mL, 4.3 mmol), triphenylphosphine (1.1 g, 4.3 mmol) and diethyl azodicarboxylate (0.69 mL, 4.3 mmol) at 0° C. The mixture was stirred for 30 min at 0° C. and for 16 h at room temperature. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel with dichloromethane: methanol 4:1 to yield the product as yellowish oil, MS (ISP) 368.0, 370.0 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography on silica gel with dichloromethane: methanol 4:1

Sources & evidence

ORD record
ord-f508436bdc4647d1a98daf46b2fa6ffa
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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