Sodium Carbonate → (S)-2-(1-((5-(3-Fluoro-5-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052681Notes

Reaction equation

HRID 1052681 reaction equation
I[C:2]1[C:3]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])=[N:4][CH:5]=[N:6][CH:7]=1.[F:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[C:33]([OH:35])[CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[F:28][C:29]1[CH:30]=[C:31]([C:2]2[C:3]([NH:8][C@H:9]([C:11]3[N:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:15](=[O:23])[C:14]4=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]4[N:12]=3)[CH3:10])=[N:4][CH:5]=[N:6][CH:7]=2)[CH:32]=[C:33]([OH:35])[CH:34]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 447173083-Fluoro-5-hydroxybenzeneboronic acidHCID 118433754(S)-2-(1-((5-Iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73776066(S)-2-(1-((5-(3-Fluoro-5-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 54.8%

Procedure

(S)-2-(1-((5-Iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (115 mg, 0.24 mmol) was treated with (3-fluoro-5-hydroxyphenyl)boronic acid (57 mg, 0.37 mmol), sodium carbonate (2M, 548 μl, 1.10 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (30 mg, 0.04 mmol) according to the method described in Example 3 to give 60 mg (54% yield) of the title compound. Purity 100%.

Sources & evidence

ORD record
ord-fc3f2d9d6da741d09a70f78a5c857ac8
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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