1,4-二溴丁烷 → 1-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile

HRID 7719

反应方程式

HRID 7719 反应方程式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([Cl:19])[CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:31][CH2:32][CH2:33][CH2:34]Br>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:17]#[N:18])[CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:12]([Cl:19])[CH:11]=1

参与物

5

反应物 3

HCID 80561,4-二溴丁烷HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10286072[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

产物 1

HCID 102865191-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

A solution of [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (270 mg, 1.0 mmol) and THF (20 mL) was cooled to −78° C. A solution of NaHMDS (3.7 mL, 2.2 mmol, 0.6M solution in PhMe) was added dropwise via syringe to the reaction. After 15 min at −78° C., 1,4-dibromobutane (143 μL, 1.2 mmol) was added dropwise via syringe. The cooling bath was removed, and the reaction was allowed to warm to rt. The reaction was quenched by the addition of silica gel (600 mg) and concentrated to dryness. The residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.34 (s, 1H), 8.12 (dd, 1H), 7.77–7.80 (m, 1H), 7.56–7.62 (m, 2H), 7.35–7.42 (m, 2H), 2.71–2.78 (m, 2H), 2.14–2.26 (m, 2H), 1.89–2.01 (m, 4H). MS (ESI) 323 (M+H)+.

后处理

  1. customThe cooling bath was removed
  2. customThe reaction was quenched by the addition of silica gel (600 mg)
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5)

来源与证据

ORD记录
ord-f11ad2c55b7f49aca6d002758dd0a103
来源数据集
uspto-grants-2006_08
专利号
US07087601B2

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