3-Acrylamidophenylboronic acid → N-(3-(2-chloro-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide

HRID 1500784Notes

Reaction equation

HRID 1500784 reaction equation
FC1N(C)CCN(C2C=CC(N[C:16]3[N:21]=[C:20]([C:22]4[CH:23]=[C:24]([NH:28][C:29](=[O:32])[CH:30]=[CH2:31])[CH:25]=[CH:26][CH:27]=4)[C:19]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=4)=[CH:18][N:17]=3)=CC=2)C1.[Cl:41]C1N=C(Cl)C(NC2C=CC=C(F)C=2)=CN=1.C(NC1C=C(B(O)O)C=CC=1)(=O)C=C>[Pd]>[Cl:41][C:16]1[N:21]=[C:20]([C:22]2[CH:23]=[C:24]([NH:28][C:29](=[O:32])[CH:30]=[CH2:31])[CH:25]=[CH:26][CH:27]=2)[C:19]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=2)=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 103213313-Acrylamidophenylboronic acidHCID 68384964N-(3-(2-((4-(3-fluoro-4-methylpiperazin-1-yl)phenyl)amino)-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamideHCID 866775172,4-dichloro-N-(3-fluorophenyl)pyrimidin-5-amine

Product 1

HCID 71469247N-(3-(2-chloro-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

As an example, N-(3-(2-((4-(3-fluoro-4-methylpiperazin-1-yl)phenyl)amino)-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide can be prepared according to Route I. Beginning with 2,4-dichloro-N-(3-fluorophenyl)pyrimidin-5-amine, a palladium catalyzed coupling reaction with (3-acrylamidophenyl)boronic acid provides N-(3-(2-chloro-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide under mild conditions. Reaction of this product with 4-(3-fluoro-4-methylpiperazin-1-yl)aniline under palladium catalyzed aminolysis conditions yields N-(3-(2-((4-(3-fluoro-4-methylpiperazin-1-yl)phenyl)amino)-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide.

Sources & evidence

ORD record
ord-c190c40262e4457eb610f57e26ab4a07
Source dataset
uspto-grants-2015_12
Patent number
US09206176B2

Reaction notes

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