Tetrahydrofuran → 2-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-benzenesulfonylmethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole

HRID 1392237Notes

Reaction equation

HRID 1392237 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[N:6]1)[CH2:2][CH:3]=[CH2:4].C1COCC1.Br[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH2:25][C:26]2[N:27]=[C:28]([C:31]3[NH:32][C:33]4[C:38]([CH:39]=3)=[CH:37][C:36]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:35][CH:34]=4)[O:29][CH:30]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.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].O>[N:5]1([CH2:1][CH2:2][CH2:3][CH2:4][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][C:26]3[N:27]=[C:28]([C:31]4[NH:32][C:33]5[C:38]([CH:39]=4)=[CH:37][C:36]([O:40][C:41]([F:44])([F:42])[F:43])=[CH:35][CH:34]=5)[O:29][CH:30]=3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:9]=[CH:8][N:7]=[N:6]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 190682081-but-3-enyl-1H-[1,2,3]triazoleHCID 1363319632-[4-(4-bromo-benzenesulfonylmethyl)-oxazol-2-yl]-5-trifluoromethoxy-1H-indole

Product 1

HCID 1353998112-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-benzenesulfonylmethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-but-3-enyl-1H-[1,2,3]triazole (69 mg, 0.56 mmol) in THF (5 ml) 9-borabicyclo[3.3.1]nonane (0.5 M in THF, 2.46 ml, 1.23 mmol) was added dropwise at 0° C. and stirring continued for 2 h. This mixture was then added to a solution of 2-[4-(4-bromo-benzenesulfonylmethyl)-oxazol-2-yl]-5-trifluoromethoxy-1H-indole (0.28 g, 0.56 mmol), Pd(dppf)Cl2 (49 mg, 0.06 mmol) and aqueous cesium carbonate (0.56 ml, 3M) in DMF (5 ml) and stirred for 3 h at 70° C. Water (10 ml) was added and the mixture extracted with ethyl acetate (3×20 ml). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified on silica gel (ethyl acetate) to yield 2-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-benzenesulfonylmethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole as light yellow solid. Yield 24 mg (8%)

Workup

  1. stirringstirred for 3 h at 70° C
  2. extractionthe mixture extracted with ethyl acetate (3×20 ml)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-cd0e8ac487304692b0f1a0f1b852a272
Source dataset
uspto-grants-2008_03
Patent number
US07342030B2

Reaction notes

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