Ethyl Acetate → 5-(1,3-Benzoxazol-2-yl)-2-pyridin-2-yl benzonitrile

HRID 7760

反応式

HRID 7760 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:8]=1[C:22]#[N:23])(=O)=O.C([Sn](CCCC)(CCCC)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)CCC.CCOC(C)=O>COCCOC.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[C:8]([CH:9]=1)[C:22]#[N:23]

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 6077842-(Tributylstannyl)pyridineHCID 219909674-(1,3-Benzoxazol-2-yl)-2-cyanophenyl trifluoromethanesulfonate

生成物 1

HCID 102364675-(1,3-Benzoxazol-2-yl)-2-pyridin-2-yl benzonitrile

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

The degassed solution of 4-(1,3-benzoxazol-2-yl)-2-cyanophenyl trifluoromethanesulfonate (300 mg, 1.2 mmol) in DME (5 mL) was added 2-tri-n-butylstannylpyridine (273 mg, 0.74 mmol), tetrakis(triphenylphosphine)palladium(0) (150 mg, 0.1 mmol). The reaction was stirred at 90° C. overnight and cooled to rt. EtOAc (100 mL) was added, as well as brine (50 mL). The organic layer was washed with brine (2×20 mL), dried (MgSO4), and the crude material was purified on flash column (silica gel, hexanes:EtOAc 3:1) to afford desired 5-(1,3-benzoxazol-2-yl)-2-pyridin-2-yl benzonitrile as pinkish solid. 1H NMR (CD3OD, 300 MHz), δ 8.85 (d 1H), 8.72 (d, 1H), 8.59 (m, 1H), 8.08 (d, 1H), 7.91 (d, 2H), 7.85 (m, 1H), 7.65 (m, 1H), 7.45 (m, 3H). MS (ESI) 298 (M+H)+.

後処理

  1. temperaturecooled to rt
  2. washThe organic layer was washed with brine (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. customthe crude material was purified on flash column (silica gel, hexanes:EtOAc 3:1)

出典と根拠

ORDレコード
ord-2b86ba7fc6984a3c8299ef5961aa3279
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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