Sodium triacetoxyborohydride → 2-Fluoro-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519600ノート

反応式

HRID 1519600 の反応式
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=1)([O-:15])=[O:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH2:11][N:27]2[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][C:19]3[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=3)[CH2:25][CH2:26]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazineHCID 866944782-Fluoro-4-(2-oxoethyl)benzonitrile

生成物 1

HCID 680713482-Fluoro-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2-fluoro-4-(2-oxoethyl)benzonitrile (140 mg, 0.88 mmol), 1-[2-(4-nitrophenyl)ethyl]piperazine (170 mg, 0.73 mmol) and NaBH(OAc)3 (620 mg, 2.9 mmol) in anhydrous DCM (10 mL) was stirred at ambient temperature overnight. The reaction was completed according to TLC. The reaction mixture was added 20 mL of DCM, washed with brine, separated the organic layer, dried over anhydrous sodium sulfate and concentrated. The residue was purified by preparative TLC to give the product. 1H-NMR (400 MHz, CDCl3) δ ppm 8.13˜8.16 (d, J=8.6 Hz, 2H), 7.52˜7.55 (t, J=6.6 Hz, 1H), 7.36˜7.38 (d, J=8.6 Hz, 2H), 7.08˜7.12 (m, 2H), 2.89˜3.00 (m, 4H), 2.56˜2.78 (m, 12H). MS m/z: 383 (M+1)+. (0.24 μM)

後処理

  1. washwashed with brine
  2. customseparated the organic layer
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC
  6. customto give the product

出典と根拠

ORDレコード
ord-4dd76851c35043ec9b9b92ac4b15d79e
出典データセット
uspto-grants-2015_07
特許番号
US09073882B2

反応ノート

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