1,4-Dibromobutane → 1-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile

HRID 7734

Reaction equation

HRID 7734 reaction equation
[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]([O:19][CH3:20])[CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:32][CH2:33][CH2:34][CH2:35]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])[CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:12]([O:19][CH3:20])[CH:11]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10192854Boma

Product 1

HCID 102366671-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile (130 mg, 0.49 mmol) in THF (5.0 mL) was cooled to −78° C. under argon atmosphere. Sodium bis(trimethylsilyl)amide (1.8 mL, 1.08 mmol) was added slowly and after fifteen minutes, added 1,4-dibromobutane (0.07 mL, 0.59 mmol) to dark brown reaction mixture. Let mixture warm to rt overnight. After concentrating reaction mixture in vacuo, the resulting pink oil was purified by flash chromatography, using a gradient elution of 1:9 EtOAc:hexanes to 1:4 EtOAc:hexanes. This afforded the desired compound, 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile, as a yellow solid. 1H NMR(CDCl3, 300 MHz) δ 7.86–7.26 (m, 7H), 4.07 (s, 3H), 2.59–1.91 (m, 8H). MS (ESI) 319.1 (M+H)+.

Workup

  1. concentrationAfter concentrating
  2. customreaction mixture in vacuo
  3. customthe resulting pink oil was purified by flash chromatography
  4. washa gradient elution of 1:9 EtOAc

Sources & evidence

ORD record
ord-34ed716cd4364862b6fb3902c6311fb6
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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