1,3-Dibromopropane → 1-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclobutanecarbonitrile

HRID 7728

Reaction equation

HRID 7728 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]([CH:16]([CH3:19])[C:17]#[N:18])=[C:12]([O:20][CH3:21])[CH:11]=1.O1C2C=CC=CC=2N=[C:23]1[C:31]1C=CC(C#N)=C(OC)C=1.BrCCCBr>>[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])[CH2:31][CH2:23][CH2:19]2)=[C:12]([O:20][CH3:21])[CH:11]=1

Participants

4

Reactant 3

HCID 80011,3-DibromopropaneHCID 101493732-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]propanenitrileHCID 219909874-(1,3-Benzoxazol-2-yl)-2-methoxybenzonitrile

Product 1

HCID 219909461-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclobutanecarbonitrile

Procedure

Utilizing the general procedure outlined in the synthesis of 2-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]propanenitrile, 4-(1,3-benzoxazol-2-yl)-2-methoxybenzonitrile (250 mg, 0.95 mmol) was reacted with 1,3-Dibromopropane (120 μL, 1.1 mmol) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclobutanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.89–7.87 (m, 3H), 7.62–7.55 (m, 1H) 7.39–7.36 (m, 2H), 7.32–7.26 (m, 1H), 4.05 (s, 3H), 2.90–2.83 (m, 2H), 2.67–2.47 (m, 4H). MS (ESI) 305 (M+H)+.

Sources & evidence

ORD record
ord-aca996cf3f944717aae7a25cfe9fad93
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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