Cesium carbonate → HCID 90041581, compound

HRID 522984Notes

Reaction equation

HRID 522984 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]2=[N:6][CH:7]=1.[CH3:26][S:27]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[C:14]([NH:13][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([NH:34][C:33]3[CH:32]=[CH:31][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:36][CH:35]=3)[N:3]=2)[N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 796174-(Methylsulfonyl)anilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 715756452-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 1

HCID 90041581HCID 90041581, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 292 μmol), 4-(methylsulfonyl)aniline (75.1 mg, 439 μmol), xantphos (50.8 mg, 87.7 μmol), Pd2(dba)3 (26.8 mg, 29.2 μmol) and cesium carbonate (191 mg, 585 μmol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled, filtered through celite, and the filtrate concentrated in vacuo. Purification by chromatography (silica, 20-75% ethyl acetate in hexanes) gave N-tert-butyl-2-(4-(methylsulfonyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 174 μmol, 59%) as a light yellow solid. (EI/CI) m/z: 518.3 [M+H].

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by chromatography (silica, 20-75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2b1491e0dc6543a0b70d79b083320af3
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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