Benzyl azide → HCID 67431375, compound

HRID 242402Notes

Reaction equation

HRID 242402 reaction equation
[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:20][C:21]1[CH:22]=[C:23]([C:28]2([C:41]([F:44])([F:43])[F:42])[O:32][N:31]=[C:30]([C:33]3[S:34][C:35]([C:39]#[CH:40])=[C:36]([CH3:38])[CH:37]=3)[CH2:29]2)[CH:24]=[C:25]([Cl:27])[CH:26]=1>CN(C=O)C.[Cu]I>[CH2:1]([N:8]1[CH:40]=[C:39]([C:35]2[S:34][C:33]([C:30]3[CH2:29][C:28]([C:23]4[CH:24]=[C:25]([Cl:27])[CH:26]=[C:21]([Cl:20])[CH:22]=4)([C:41]([F:44])([F:43])[F:42])[O:32][N:31]=3)=[CH:37][C:36]=2[CH3:38])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 12152Benzyl azideHCID 81531DiisopropylethylamineHCID 86685437HCID 86685437, compound

Product 1

HCID 67431375HCID 67431375, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

CuI (47 mg) is added to a solution of benzylazide (33 mg), DIPEA (1.05 ml) and 5-(3,5-dichloro-phenyl)-3-(5-ethynyl-4-methyl-thiophen-2-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole (100 mg) in DMF (2.0 ml). After 16 hours at room temperature, the reaction is quenched with a saturated aqueous solution of NaHCO3 and extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 1-benzyl-4-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-1H-[1,2,3]triazole (34 mg) as a yellowish foam. MS (HPLC/MS): 537 (MH+). Retention time: 5.04 min.

Workup

  1. customthe reaction is quenched with a saturated aqueous solution of NaHCO3
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-3cefc72a49e24db88a3d2a47e0725be0
Source dataset
uspto-grants-2014_02
Patent number
US08653116B2

Reaction notes

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