Sodium Carbonate → (S)-N-(4-(4-((1-(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)-1H-indol-6-yl)methanesulfonamide

HRID 1052481Notes

Reaction equation

HRID 1052481 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=[CH:27][CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:3]=1.CC1(C)C(C)(C)OB([C:46]2[CH:54]=[C:53]([NH:55][S:56]([CH3:59])(=[O:58])=[O:57])[CH:52]=[C:51]3[C:47]=2[CH:48]=[CH:49][NH:50]3)O1.CS(N)(=O)=O.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:26]=[C:18]1[C:17]2=[CH:27][CH:28]=[CH:29][N:16]2[N:15]=[C:14]([C@@H:12]([NH:11][C:9]2[C:10]3[C:2]([C:46]4[CH:54]=[C:53]([NH:55][S:56]([CH3:59])(=[O:57])=[O:58])[CH:52]=[C:51]5[C:47]=4[CH:48]=[CH:49][NH:50]5)=[CH:3][N:4]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:5]=3[N:6]=[CH:7][N:8]=2)[CH3:13])[N:19]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 72879MethanesulfonamideHCID 2733548Bis(pinacolato)diboraneHCID 131736160(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneHCID 131736163N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-6-yl)methanesulfonamide

Product 1

HCID 131736162(S)-N-(4-(4-((1-(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)-1H-indol-6-yl)methanesulfonamideYield 98%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (125 mg, 0.22 mmol) was treated with N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-6-yl)methanesulfonamide (187 mg, 0.56 mmol, prepared from N-(4-bromo)-1H-indol-6-yl)methanesulfonamide, which is described at WO 2009147188 A1 20091210, and bis(pinacolato)diboron according to Preparation 119b), sodium carbonate (60 mg, 0.57 mmols) and bis(triphenylphosphine)palladium(II) dichloride (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 152 mg (98% yield) of the title compound. Purity 98%.

Workup

  1. customdescribed in Preparation 62
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 80%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-aeed10adad67490f901c0adc5828fd89
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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