1,5-Dibromopentane → 1-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclohexanecarbonitrile

HRID 7729

Reaction equation

HRID 7729 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]([C:16]2([C:20]#[N:21])[CH2:19][CH2:18][CH2:17]2)=[C:12]([O:22][CH3:23])[CH:11]=1.O1C2C=CC=CC=2N=[C:25]1[C:33]1C=CC(C#N)=C(OC)C=1.BrCCCCCBr>>[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:20]#[N:21])[CH2:17][CH2:18][CH2:19][CH2:33][CH2:25]2)=[C:12]([O:22][CH3:23])[CH:11]=1

Participants

4

Reactant 3

HCID 81001,5-DibromopentaneHCID 219909461-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclobutanecarbonitrileHCID 219909874-(1,3-Benzoxazol-2-yl)-2-methoxybenzonitrile

Product 1

HCID 101258311-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclohexanecarbonitrile

Procedure

Utilizing the general procedure outlined for the synthesis of 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclobutanecarbonitrile, 4-(1,3-benzoxazol-2-yl)-2-methoxybenzonitrile (250 mg, 0.95 mmol) was reacted with 1,5-dibromopentane (160 μL, 1.1 mmol) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclohexanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.83–7.75 (m, 3H), 7.59–7.56 (m, 1H) 7.45–7.43 (d, 1H), 7.38–7.34 (m, 2H), 4.04 (s, 3H), 2.41–2.38 (d, 2H), 1.92–1.15 (m, 8H). MS (ESI) 333 (M+H)+.

Sources & evidence

ORD record
ord-7b79bebf58c34dd69f3bb212bdae195b
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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