4,7-Dichloro-3-iodoquinoline → HCID 89690238, compound

HRID 1771108Notes

Reaction equation

HRID 1771108 reaction equation
C(NCCCN[C:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)(C)(C)C.[Cl:32]C1C2C(=CC(Cl)=CC=2)N=CC=1I>ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd+2]>[Cl:32][C:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 124985044,7-Dichloro-3-iodoquinolineHCID 66556492HCID 66556492, compound

Product 1

HCID 89690238HCID 89690238, compound

Reagents, catalysts & solvents 2

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)CatalystHCID 178478229HCID 178478229, compoundCatalyst

Procedure

Alternatively, compound 1 can be synthesized according to Scheme 2 by performing the Suzuki coupling directly on the 4-chloro 3-iodo quinoline (C) using dichloro [1,1′ bis(diphenylphosphino)ferrocene)]palladium (II) [PdCl2(dppf)] (Hayashi, T. J. Am. Chem. Soc. 1984, 106, 158-163, incorporated by reference herein) as a catalyst to give 4,7-dichloro-3-(4-(trifluoromethoxy)phenyl)quinoline (P) in 79% yield a white solid after flash chromatography. Finally, the desired product compound 1 is obtained using the same procedure as described in Scheme 2 in approximately 90% yield. In some embodiments, this new and more efficient method (Scheme 2) may give an overall yield of approximately 42%.

Sources & evidence

ORD record
ord-86a013c0b33d4bbfafe91ba61dd8908e
Source dataset
uspto-grants-2016_02
Patent number
US09249103B2

Reaction notes

Loading…