Benzyl azide → HCID 67431375, compound

HRID 2167004Notes

Reaction equation

HRID 2167004 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-84ad3bf39ade445c8ed4fa37b350224e
Source dataset
uspto-grants-2015_06
Patent number
US09044389B2

Reaction notes

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