Azetidine → HCID 123897862, compound

HRID 1054936Notes

Reaction equation

HRID 1054936 reaction equation
Br[C:2]1[N:6]=[C:5]([CH:7]=[CH:8][C:9]2[N:19]=[C:12]3[C:13]([CH3:18])=[N:14][CH:15]=[C:16]([CH3:17])[N:11]3[N:10]=2)[N:4]([CH3:20])[N:3]=1.[O-]C1C=CC=CC=1.[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[NH:71]1[CH2:74][CH2:73][CH2:72]1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl>[N:71]1([C:2]2[N:6]=[C:5]([CH:7]=[CH:8][C:9]3[N:19]=[C:12]4[C:13]([CH3:18])=[N:14][CH:15]=[C:16]([CH3:17])[N:11]4[N:10]=3)[N:4]([CH3:20])[N:3]=2)[CH2:74][CH2:73][CH2:72]1

Participants

7

Reactant 4

HCID 10422AzetidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4445035Phenolate SodiumHCID 123587010HCID 123587010, compound

Product 1

HCID 123897862HCID 123897862, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (28 mg, 83.8 μmol, Eq: 1.00) in dioxane (1 ml) was purged with argon, then sodium phenoxide (14.6 mg, 126 μmol, Eq: 1.5), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xant-phos) (3.88 mg, 6.7 μmol, Eq: 0.08), tris(dibenzylideneacetone)dipalladium chloroform complex/Pd2(dba)3CHCl3 (3.47 mg, 3.35 μmol, Eq: 0.04) and azetidine (9.57 mg, 11.3 μl, 168 μmol, Eq: 2) were added. The vial was capped and irradiated at 140° C. for 30 minutes in the microwave oven. The crude material was applied on silicagel and purified by chromatography over a 5 g silicagel column using ethyl acetate/methanol 0-10% as eluent affording 2-[2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (4 mg/15.4%) as a light yellow solid. MS: m/e=311.4 (M+H+)

Workup

  1. customThe vial was capped
  2. customirradiated at 140° C. for 30 minutes in the microwave oven
  3. custompurified by chromatography over a 5 g silicagel column

Sources & evidence

ORD record
ord-d106a6ce17f24035810edb9c2cd512b0
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…