Cesium carbonate → HCID 86726511, compound

HRID 1487684Notes

Reaction equation

HRID 1487684 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:5]2[C:10]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([NH:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:6]=2[N:7]=1.[CH3:36][N:37]1[C:41]([NH2:42])=[CH:40][CH:39]=[N:38]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO>[CH3:18][NH:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([C:10]2[C:5]3[C:4]([O:29][CH:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[N:3][C:2]([NH:42][C:41]4[N:37]([CH3:36])[N:38]=[CH:39][CH:40]=4)=[N:7][C:6]=3[N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:26])[CH3:27])[CH:9]=2)=[CH:12][CH:13]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86726510HCID 86726510, compound

Product 1

HCID 86726511HCID 86726511, compoundYield 39.4%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(2-chloro-4-((tetrahydro-2H-pyran-4-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide (1 equiv), 1-methyl-1H-pyrazol-5-amine (1 equiv), and cesium carbonate (3 equiv) in 1,4-dioxane (0.1 M) was degassed with N2 for 10 min. Then (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.2 equiv), tris(dibenzylideneacetone)dipalladium(0) (0.1 equiv), were added to this mixture. The mixture was stirred at 140° C. for 1.5 h. After cooling to room temperature the reaction mixture was purified using flash chromatography (0-100% ethyl acetate in hexane then 0-20% MeOH in DCM) to give the title compound (39.4% yield) as an off white solid. MS (ESI) m/z 578.5 [M+1]+.

Workup

  1. customwas degassed with N2 for 10 min
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. customwas purified

Sources & evidence

ORD record
ord-e5a06e0668c24785849f6ff37a3f9c8a
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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