Toluene → HCID 57786272、化合物

HRID 1399348ノート

反応式

HRID 1399348 の反応式
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.CC(C)([O-])C.[K+]>C(#N)C.C(OCC)(=O)C.O1CCCC1>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:19]1[C:6]2=[N:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:9]=3[N:5]2[CH2:4][CH2:3][CH:2]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 23665647Potassium tert-butoxideHCID 68775340HCID 68775340、化合物

生成物 1

HCID 57786272HCID 57786272、化合物収率 23%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of [1-(3-bromopropyl)-7-(diethylamino)-1H-benzimidazol-2-yl](2,4-dichlorophenyl)methanone (Reference example 211, 360 mg, 0.745 mmol) and triphenylphosphine (586 mg, 2.23 mmol) in acetonitrile (5 mL) was stirred for 60 h at 80° C. The reaction mixture was concentrated in vacuo. Toluene (5 mL), tetrahydrofuran (1 mL), and potassium tert-butoxide (85%, 83.6 mg, 0.745 mmol) was added at room temperature. After 1 h, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture to afford the desired product as pale yellow solid (65.5 mg, 0.170 mmol, 23%).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-012e506bb28b4723b323370bbf12ea14
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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