Triphenylphosphine → tert-Butyl 2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl(methyl)carbamate

HRID 517997Notes

Reaction equation

HRID 517997 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([OH:8])=[N:6][CH:7]=1.O[CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[C:5]([O:8][CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 178517592HCID 178517592, compound

Product 1

HCID 69931961tert-Butyl 2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl(methyl)carbamateYield 76.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 5-bromo-3-(trifluoromethyl)pyridin-2-ol (500 mg) in 1,4-dioxane (10 ml), tert-butyl 2-hydroxyethyl(methyl)carbamate (475 mg) and triphenylphosphine (684 mg) were added. Then diisopropyl azodicarboxylate (556 mg) was dropwised and stirred at 20° C. for 1.5 h. The mixture was evaporated off the solvent and purified by Biotage SNAP cartridge KP-Sil column (50 g, heptane:ethyl acetate=1:0, 5:1, 4:1, 3:1 to 2:1) to give 630 mg yellow oil as tert-butyl 2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl(methyl)carbamate (76%).

Workup

  1. additionwere added
  2. customThe mixture was evaporated off the solvent
  3. custompurified by Biotage SNAP cartridge KP-Sil column (50 g, heptane:ethyl acetate=1:0, 5:1, 4:1, 3:1 to 2:1)

Sources & evidence

ORD record
ord-383a6150ab9b4ef3920ee0678b352e43
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

Loading…