Dietylaminopropin → 4-(3-Diethylamino-prop-1-ynyl)-3-methoxy-benzonitrile

HRID 451279Notes

Reaction equation

HRID 451279 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C2C=CC=CC=2)(=O)=O)=[C:5]([O:19][CH3:20])[CH:4]=1)#[N:2].[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][C:25]#[CH:26])[CH3:22]>CCCCCCC.CCOC(C)=O>[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][C:25]#[C:26][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[O:19][CH3:20])[CH3:22]

Participants

4

Reactant 2

HCID 20010DietylaminopropinHCID 24235536Benzenesulfonic acid 4-cyano-2-methoxy-phenyl ester

Product 1

HCID 252218324-(3-Diethylamino-prop-1-ynyl)-3-methoxy-benzonitrile

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from benzene-sulfonic acid 4-cyano-2-methoxy-phenyl ester and diethyl-prop-2-ynyl-amine following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 1:1; yield (90 mg, 74%); 1H NMR δ (CDCl3): 7.52 (d, J=8.35 Hz, 1H), 7.21 (d, J=8.21 Hz, 1H), 7.11 (s, 1H), 3.81 (s, 3H), 2.69 (t, J=7.22 Hz, 2H), 2.58 (t, J=7.21 Hz, 2H), 1.99 (p, J=7.11 Hz, 2H); LCMS m/z: 242.

Workup

  1. customyield (90 mg, 74%)

Sources & evidence

ORD record
ord-0c275849213b4564a2aafdbd314882f8
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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