6-Chloronicotinoyl Chloride → HCID 59318055, compound

HRID 2190536Notes

Reaction equation

HRID 2190536 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:6][C:7]=1[NH2:8].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][N:19]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>CCOC(C)=O>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=3[F:16])=[CH:3][C:2]=2[F:1])=[O:23])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamideHCID 593181633,2',4'-Trifluoro-biphenyl-4-ylamine

Product 1

HCID 59318055HCID 59318055, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-N-(3,2′,4′-trifluoro-biphenyl-4-yl)-nicotinamide was prepared from 3,2′,4′-trifluoro-biphenyl-4-yl amine and 6-chloronicotinoyl chloride following a procedure similar to the one described in the synthesis of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide, above. The product was isolated after a silica gel column chromatography with 0-30% EtOAc in hexanes. H1 NMR (300 MHz, chloroform-d) d ppm 6.91 (m, 2H), 7.15 (apparent t, J=8.1 Hz, 1H), 7.24-7.1 (m, 3H), 7.95 (dd, J=10.5 8.1 Hz, 2H), 8.69 (d, J=2.1 Hz, 2H).

Sources & evidence

ORD record
ord-a84197496ab44f699decf74b13cfd7ee
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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