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

HRID 1052665Notes

Reaction equation

HRID 1052665 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=[CH:24][CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])=[N:4][CH:5]=[N:6][CH:7]=1.[F:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[C:32]([OH:34])[CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[F:27][C:28]1[CH:29]=[C:30]([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=[CH:24][CH:25]=[CH:26][N:13]4[N:12]=3)[CH3:10])=[N:4][CH:5]=[N:6][CH:7]=2)[CH:31]=[C:32]([OH:34])[CH:33]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 447173083-Fluoro-5-hydroxybenzeneboronic acidHCID 118433847(S)-2-(1-((5-Iodopyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73774798(S)-2-(1-((5-(3-Fluoro-5-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 52%

Procedure

(S)-2-(1-((5-Iodopyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (30 mg, 0.07 mol) was treated with (3-fluoro-5-hydroxyphenyl)boronic acid (15 mg, 0.10 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (87 mg, 0.1 mmol) and sodium carbonate (2M, 147 μl, 0.29 mol) according to the method described in Example 3 to give 15 mg (52% yield) of the title compound as a white solid. Purity 99%.

Sources & evidence

ORD record
ord-970b72f7f41f49d3a4da1641810f3479
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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