Diisopropylethylamine → HCID 46842399, compound

HRID 388374Notes

Reaction equation

HRID 388374 reaction equation
[N:1]([CH2:4][C:5]1[N:10]=[CH:9][CH:8]=[CH:7]N=1)=[N+:2]=[N-:3].[CH:11](N(CC)C(C)C)(C)C.[Cl:20][C:21]1[CH:22]=[C:23]([C:28]2([C:45]([F:48])([F:47])[F:46])[O:32][N:31]=[C:30]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:36]([C:43]#[CH:44])=[CH:35][CH:34]=3)[CH2:29]2)[CH:24]=[C:25]([Cl:27])[CH:26]=1>CN(C=O)C.[Cu]I>[Cl:20][C:21]1[CH:22]=[C:23]([C:28]2([C:45]([F:46])([F:48])[F:47])[O:32][N:31]=[C:30]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:36]([C:43]4[N:3]=[N:2][N:1]([CH2:4][C:5]5[CH:11]=[CH:7][CH:8]=[CH:9][N:10]=5)[CH:44]=4)=[CH:35][CH:34]=3)[CH2:29]2)[CH:24]=[C:25]([Cl:27])[CH:26]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 62699014HCID 62699014, compoundHCID 86658158HCID 86658158, compound

Product 1

HCID 46842399HCID 46842399, compound

Reagents, catalysts & solvents 2

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

Procedure

CuI (88 mg) is added to a solution of 2-azidomethyl-pyrimidine (62 mg), N,N-diisopropylethylamine (DIPEA, 2.0 ml) and 5-(3,5-dichloro-phenyl)-3-(4-ethynyl-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole (100 mg) in DMF (1.0 ml). After 16 hours at room temperature, the reaction is quenched with a saturated solution of NaHCO3 and extracted with dichloromethane. The combined organic phases are dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 2-(4-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-[1,2,3]triazol-1-ylmethyl)-pyridine as a beige foam. (compound 1.27, Table 1).

Workup

  1. customthe reaction is quenched with a saturated solution of NaHCO3
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-3ebc3c810c7b4a569c45952fc79f12b4
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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