Sodium Carbonate → HCID 73776369, compound

HRID 1052757Notes

Reaction equation

HRID 1052757 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.[F:29][CH:30]([F:46])[C:31]1[CH:32]=[N:33][CH:34]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:36]=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:35]1[CH:34]=[N:33][CH:32]=[C:31]([CH:30]([F:46])[F:29])[CH:36]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 595349743-(Difluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 118433733HCID 118433733, compound

Product 1

HCID 73776369HCID 73776369, compoundYield 3.4%

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 (81 mg, 0.18 mmol) was treated with 3-(difluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (237 mg, 0.93 mmol, prepared according to WO2012/087237), sodium carbonate (2M, 700 μl, 1.40 mmol) and 1,1-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (20 mg, 0.02 mmol) according to the method described in Example 3 to give 3 mg (3% yield) of the title compound. Purity 98%.

Sources & evidence

ORD record
ord-4c0665148b4b4076aa3ad9c72ece169c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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