5-Bromo-2-ethoxypyridine → 2-Ethoxy-5-{4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}pyridine

HRID 1896026Notes

Reaction equation

HRID 1896026 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]([C:17]3[C:26]4[C:21](=CC=CC=4)[CH:20]=[N:19][CH:18]=3)[CH2:13][CH2:12]2)[CH:5]=[CH:4][CH:3]=1.BrC1C=[CH:30][C:31]([O:34]CC)=NC=1.C1(C)C=CC(P(C2C=CC(C)=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1>>[CH2:31]([O:34][C:20]1[CH:21]=[CH:26][C:17]([N:14]2[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:16][CH2:15]2)=[CH:18][N:19]=1)[CH3:30]

Participants

4

Reactant 3

HCID 8172375-Bromo-2-ethoxypyridineHCID 4189906(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthylHCID 875511624-{4-[3-(6-Methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}isoquinoline

Product 1

HCID 875508092-Ethoxy-5-{4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}pyridineYield 10%

Procedure

Following the procedure reported for the compound of Example 234 and using 5-bromo-2-ethoxypyridine instead of 4-bromoisoquinoline and tol-BINAP (2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl) instead of BINAP the title compound was prepared. After the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc 8:2. affording the title product as a yellow oil. Yield: 10%.

Sources & evidence

ORD record
ord-46756c0dec4f4e429336862cd829b958
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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