2-Methoxyphenylboronic acid → 4-{(E)-2-[5-(2-Methoxyphenyl)pyridin-2-yl]vinyl}-2-methyloctahydropyrrolo[3,4-a]-indolizine-1,3-dione

HRID 540643Notes

Reaction equation

HRID 540643 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][CH:24]=[C:23](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:54](=[O:55])C23)=NC=1.COC1C=CC=CC=1B(O)O>>[CH3:54][O:55][C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:18]1[CH:19]=[CH:20][C:15](/[CH:14]=[CH:13]/[CH:6]2[N:7]3[CH:12]([CH2:11][CH2:10][CH2:9][CH2:8]3)[CH:4]3[C:3](=[O:33])[N:2]([CH3:1])[C:31](=[O:32])[CH:5]23)=[N:16][CH:17]=1

Participants

4

Reactant 3

HCID 27339582-Methoxyphenylboronic 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 534925054-{(E)-2-[5-(2-Methoxyphenyl)pyridin-2-yl]vinyl}-2-methyloctahydropyrrolo[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 18 mg of 2-methoxyphenylboronic acid.

Sources & evidence

ORD record
ord-9789b3df6a964cff8c596ca8b1d1f642
Source dataset
uspto-grants-2014_10
Patent number
US08871798B2

Reaction notes

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