Cesium carbonate → HCID 90102850, compound

HRID 1052804Notes

Reaction equation

HRID 1052804 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][C:30]1[CH:35]=[C:34]([OH:36])[CH:33]=[CH:32][C:31]=1[S:37]([N:40]1[C:48]2[C:43](=[C:44]([OH:52])[CH:45]=[C:46](B(O)O)[CH:47]=2)[CH:42]=[CH:41]1)(=[O:39])=[O:38].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C>[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:46]1[CH:47]=[C:48]2[C:43]([CH:42]=[CH:41][N:40]2[S:37]([C:31]2[CH:32]=[CH:33][C:34]([OH:36])=[CH:35][C:30]=2[F:29])(=[O:38])=[O:39])=[C:44]([OH:52])[CH:45]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 118433733HCID 118433733, compoundHCID 131736270HCID 131736270, compound

Product 1

HCID 90102850HCID 90102850, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (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 (28 mg, 0.06 mmol) were added (1-((2-fluoro-4-hydroxyphenyl)sulfonyl)-4-hydroxy-1H-indol-6-yl)boronic acid (22 mg, 0.06 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (5 mg, 0.01 mmol) and 63 μl of a 2M aqueous solution of cesium carbonate in dioxane (2 ml). The mixture was stirred under argon atmosphere at 100° C. for 18 hours and then diluted with ethyl acetate. The resulting solution was washed with water and brine, dried over magnesium sulphate, filtered and the solvents were removed under reduced pressure. The product was purified by reverse phase using SP1® Purification System to give 8 mg (19% yield) as a white solid. Purity 99%.

Workup

  1. washThe resulting solution was washed with water and brine
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customThe product was purified by reverse phase
  6. custom® Purification System
  7. customto give 8 mg (19% yield) as a white solid

Sources & evidence

ORD record
ord-914fc7797e544f559965c9746bfb0011
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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