Sodium Carbonate → HCID 118433910, compound

HRID 1052755Notes

Reaction equation

HRID 1052755 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([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])[C:3]=1Br.[OH:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[C:34]([O:36][C:37]([F:40])([F:39])[F:38])[CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([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])[C:3]=1[C:32]1[CH:33]=[C:34]([O:36][C:37]([F:40])([F:38])[F:39])[CH:35]=[C:30]([OH:29])[CH:31]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 44717692[3-Hydroxy-5-(trifluoromethoxy)phenyl]boronic acidHCID 118433733HCID 118433733, compound

Product 1

HCID 118433910HCID 118433910, compoundYield 51%

Procedure

(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (82 mg, 0.19 mmol) was treated with 3-hydroxy-5-(trifluoromethoxy)phenylboronic acid (124 mg, 0.56 mmol), sodium carbonate (2M, 375 μl, 0.75 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (15 mg, 0.02 mmol) according to the method described in Example 3 to give 52 mg (51% yield) of the title compound. Purity 98%.

Sources & evidence

ORD record
ord-7337bfac74bd44ab8a71ab2e86c1a701
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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