Triethylamine → HCID 68595158, compound

HRID 220491Notes

Reaction equation

HRID 220491 reaction equation
[CH2:1]([C:3]1[C:7]([CH2:8][CH2:9]O)=[C:6]([CH2:11][CH3:12])[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:4]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39].C(N(CC)CC)C>C(Cl)Cl.C(OCC)C>[Br:39][CH2:9][CH2:8][C:7]1[C:3]([CH2:1][CH3:2])=[N:4][N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:6]=1[CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68595861HCID 68595861, compound

Product 1

HCID 68595158HCID 68595158, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Combine 2-(3,5-diethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-ethanol (0.68 g, 2.78 mmol) and triphenylphosphine (1.09 g, 4.18 mmol) in DCM (20 mL) and cool to 0° C. Add a solution of carbon tetrabromide (1.39 g, 4.18 mmol) and triethylamine (0.77 mL, 5.56 mmol) in DCM (5 mL) dropwise. Warm the reaction mixture to room temperature and stir for 3 hr. Dilute with diethyl ether (20 mL) and filter. Concentrate filtrate and purify using silica gel chromatography, eluting with 90:10 hexanes:ethyl acetate, to give the title preparation as an oil (0.8 g, 93%): 1H-NMR (400 MHz, CDCl3) δ 8.39 (m, 1H), 7.80 (m, 1H), 7.75 (m, 1H), 7.15 (m, 1H), 3.39 (m, 2H), 3.08 (q, 2H), 2.98 (m, 2H), 2.64 (q, 2H), 1.28 (t, 3H), 1.15 (t, 3H).

Workup

  1. filtrationfilter
  2. customConcentrate filtrate and purify
  3. washeluting with 90:10 hexanes
  4. customethyl acetate, to give the title

Sources & evidence

ORD record
ord-41b48b25fdcf4d96abed2015a01cea52
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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