Cesium carbonate → 1-[4-(4-{2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazole

HRID 750980Notes

Reaction equation

HRID 750980 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[N:6]1)[CH2:2][CH:3]=[CH2:4].B1C2CCCC1CCC2.Br[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH2:29][C:30]2[N:31]=[C:32]([CH:35]=[CH:36][C:37]3[CH:42]=[CH:41][C:40]([S:43]([C:45]([F:48])([F:47])[F:46])=[O:44])=[CH:39][CH:38]=3)[O:33][CH:34]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C>[F:48][C:45]([F:46])([F:47])[S:43]([C:40]1[CH:39]=[CH:38][C:37]([CH:36]=[CH:35][C:32]2[O:33][CH:34]=[C:30]([CH2:29][S:26]([C:23]3[CH:22]=[CH:21][C:20]([CH2:4][CH2:3][CH2:2][CH2:1][N:5]4[CH:9]=[CH:8][N:7]=[N:6]4)=[CH:25][CH:24]=3)(=[O:27])=[O:28])[N:31]=2)=[CH:42][CH:41]=1)=[O:44]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 190682081-but-3-enyl-1H-[1,2,3]triazoleHCID 692919084-(4-Bromo-benzenesulfonylmethyl)-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole

Product 1

HCID 692901901-[4-(4-{2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazoleYield 55.9%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-but-3-enyl-1H-[1,2,3]triazole (0.14 g, 1.14 mmol) in anhydrous THF (10 ml) was treated with 9-BBN (0.5 M in THF, 5 ml, 2.5 mmol) at 0° C. and stirred for 2 h at room temperature. This mixture was added to a solution of 4-(4-bromo-benzenesulfonylmethyl)-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole (0.6 g, 1.15 mmol), [Pd(dppf)Cl2] (98 mg, 0.12 mmol) and aqueous cesium carbonate (3M, 1.15 ml, 3.45 mmol) in N,N-dimethyl formamide (7 ml) and stirred for 3 h at 70° C. After cooling to room temperature ethyl acetate (100 ml) was added and the solution washed with water (2×50 ml). The organic layer was concentrated and the crude product purified by flash column chromatography (ethyl acetate) and crystallization from diethyl ether to yield 1-[4-(4-{2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazole as white solid (0.36 g, 55%).

Workup

  1. stirringstirred for 3 h at 70° C
  2. additionwas added
  3. washthe solution washed with water (2×50 ml)
  4. concentrationThe organic layer was concentrated
  5. customthe crude product purified by flash column chromatography (ethyl acetate) and crystallization from diethyl ether

Sources & evidence

ORD record
ord-2375a405d4b14ce3a2d99483c727b250
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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