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

HRID 1392237ノート

反応式

HRID 1392237 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-cd0e8ac487304692b0f1a0f1b852a272
出典データセット
uspto-grants-2008_03
特許番号
US07342030B2

反応ノート

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