Thiophene-3-boronic acid → 2-Methyl-4-[(E)-2-(5-thiophen-3-ylpyridin-2-yl)vinyl]octahydropyrrolo[3,4-a]indolizine-1,3-dione

HRID 540645Notes

Reaction equation

HRID 540645 reaction equation
[CH3:1][N:2]1[C:31](=[O:32])[CH:5]2[CH:6](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25]C=C(C(F)(F)F)[CH:22]=4)=[CH:17][N:16]=3)[N:7]3[CH:12]([CH:4]2[C:3]1=[O:33])[CH2:11][CH2:10][CH2:9][CH2:8]3.BrC1C=CC(/C=C/C2N3C(CCCC3)C3C(=O)N(C)C(=O)C23)=NC=1.[S:58]1C=CC(B(O)O)=C1>>[CH3:1][N:2]1[C:31](=[O:32])[CH:5]2[CH:6](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][S:58][CH:22]=4)=[CH:17][N:16]=3)[N:7]3[CH:12]([CH:4]2[C:3]1=[O:33])[CH2:11][CH2:10][CH2:9][CH2:8]3

Participants

4

Reactant 3

HCID 581760Thiophene-3-boronic acidHCID 534923684-[(E)-2-(5-bromopyridin-2-yl)vinyl]-2-methyloctahydropyrrolo[3,4-a]-indolizine-1,3-dione2×HCID 534925042-Methyl-4-{(E)-2-[5-(3-trifluoromethyl phenyl)pyridin-2-yl]vinyl}octahydropyrrolo[3,4-a]indolizine-1,3-dione

Product 1

HCID 534925672-Methyl-4-[(E)-2-(5-thiophen-3-ylpyridin-2-yl)vinyl]octahydropyrrolo[3,4-a]indolizine-1,3-dione

Procedure

The title compound is prepared analogously to the compound from Example 17 from 42 mg of 4-[(E)-2-(5-bromopyridin-2-yl)vinyl]-2-methyloctahydropyrrolo[3,4-a]-indolizine-1,3-dione (from Example 6, racemic mixture 3) and 15 mg of 3-thiophene-boronic acid.

Sources & evidence

ORD record
ord-ed6b7522708b46f18216da766e191456
Source dataset
uspto-grants-2014_10
Patent number
US08871798B2

Reaction notes

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