2-Bromothiophene-3-carbonitrile → 2-{4-[3-(6-Methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}thiophene-3-carbonitrile

HRID 1896025Notes

Reaction equation

HRID 1896025 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][N:14](C3C4C(=CC=CC=4)C=NC=3)[CH2:13][CH2:12]2)[CH:5]=[CH:4][CH:3]=1.Br[C:28]1[S:29][CH:30]=[CH:31][C:32]=1[C:33]#[N:34]>>[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:28]3[S:29][CH:30]=[CH:31][C:32]=3[C:33]#[N:34])[CH2:15][CH2:16]2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 120790262-Bromothiophene-3-carbonitrileHCID 875511624-{4-[3-(6-Methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}isoquinoline

Product 1

HCID 251817872-{4-[3-(6-Methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}thiophene-3-carbonitrileYield 22%

Procedure

Following the procedure reported for the compound of Example 234 and using 2-bromo-3-cyanothiophene instead of 4-bromoisoquinoline the title compound was prepared. Purification was done by RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient affording the compound of the title. Yield: 22%.

Sources & evidence

ORD record
ord-ff96c0d047d34df3874e7ae62188f3f8
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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