1-Methylpyrrole-2-carbonitrile → 5-(8-Hydroxy-2-methyl-quinolin-4-yl)-1-methyl-1H-pyrrole-2-carbonitrile

HRID 1959611Notes

Reaction equation

HRID 1959611 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH3:14][N:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]#[N:21].CC1C=C(C2N(C)C=CN=2)C2C(=C(O)C=CC=2)N=1.[Li+].CC([N-]C(C)C)C>CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[C:19]1[N:15]([CH3:14])[C:16]([C:20]#[N:21])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 20641111-Methylpyrrole-2-carbonitrileHCID 2724682Lithium diisopropylamideHCID 670771594-Bromo-2-methyl-quinolin-8-olHCID 1359503062-Methyl-4-(1-methyl-1H-imidazol-2-yl)-quinolin-8-ol

Product 1

HCID 670772535-(8-Hydroxy-2-methyl-quinolin-4-yl)-1-methyl-1H-pyrrole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Procedure

Coupling of 4-bromo-2-methyl-quinolin-8-ol (75 mg. 0.32 mmol) with 1-methyl-1H-pyrrole-2-carbonitrile (84 mg. 0.79 mmol) according to the synthesis of of 2-methyl-4-(1-methyl-1H-imidazol-2-yl)-quinolin-8-ol using LDA as the base (1.8 M in Heptan/THF/Ethylbenzol. 0.44 mL. 0.79 mmol) yielded the title compound. MS (m/z): 264.2 [M+H+].

Sources & evidence

ORD record
ord-e72e083a99e740a69e43d07ee6d4f343
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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