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

HRID 1768081Notes

Reaction equation

HRID 1768081 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]([F:48])([F:47])([F:46])([F:45])[F: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:45][S:43]([F:44])([F:46])([F:47])([F:48])[C:40]1[CH:41]=[CH:42][C:37]([CH:36]=[CH:35][C:32]2[O:33][CH:34]=[C:30]([CH2:29][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH2:4][CH2:3][CH2:2][CH2:1][N:5]4[CH:9]=[CH:8][N:7]=[N:6]4)=[CH:21][CH:22]=3)(=[O:28])=[O:27])[N:31]=2)=[CH:38][CH:39]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 190682081-but-3-enyl-1H-[1,2,3]triazoleHCID 866005064-(4-Bromo-benzenesulfonylmethyl)-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

Product 1

HCID 729684501-[4-(4-{2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazoleYield 57%

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 (80 mg, 0.65 mmol) in anhydrous THF (5 ml) was treated with 9-BBN (0.5 M in THF, 2.86 ml, 1.43 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-pentafluorosulfanyl-phenyl)-vinyl]-oxazole (345 mg, 0.65 mmol), [Pd(dppf)Cl2] (57 mg, 0.07 mmol) and aqueous cesium carbonate (3M, 0.65 ml, 1.95 mmol) in N,N-dimethyl formamide (4 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-pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazole as white solid (213 mg, 57%).

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-d494c8ceda5e4344844e7d68e8490541
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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