Cesium carbonate → (S)-3-(4-((1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-5-(methylsulfonamido)phenyl methanesulfonate

HRID 1052495Notes

Reaction equation

HRID 1052495 reaction equation
Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:14]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18](=[O:26])[C:17]4=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=1.[CH3:39][S:40]([O:43][C:44]1[CH:49]=[C:48](B2OC(C)(C)C(C)(C)O2)[CH:47]=[C:46]([NH:59][S:60]([CH3:63])(=[O:62])=[O:61])[CH:45]=1)(=[O:42])=[O:41].CS(Cl)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.[Pd](Cl)Cl>[CH3:39][S:40]([O:43][C:44]1[CH:45]=[C:46]([NH:59][S:60]([CH3:63])(=[O:62])=[O:61])[CH:47]=[C:48]([C:2]2[C:10]3[C:9]([NH:11][C@H:12]([C:14]4[N:19]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:18](=[O:26])[C:17]5=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]5[N:15]=4)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=2)[CH:49]=1)(=[O:41])=[O:42]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 901035453-(Methylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonateHCID 131736122(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 131736171(S)-3-(4-((1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-5-(methylsulfonamido)phenyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (170 mg, 0.29 mmol) was treated with 3-(methylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonate (300 mg, 0.67 mmol, prepared from the title compound of Preparation 105 and methanesulfonyl chloride according to Preparation 37), 2M cesium carbonate (450 μl, 0.90 mmols) and bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane (50 mg, 0.06 mmol) according to the method described in Preparation 62. The residue was purified using SP1® Purification System (0% to 80%, hexane-ethyl acetate) to give 169 mg (66% yield) of the title compound. Purity 87%.

Sources & evidence

ORD record
ord-4b333b6fde6c4a678baf145cdcf3b1ce
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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