Cesium carbonate → HCID 86696903, compound

HRID 1399993Notes

Reaction equation

HRID 1399993 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([C:22]3C=N[C:25]([C:28]([OH:31])(C)[CH3:29])=[N:26][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].Cl[C:33]1[N:34]=CC(C(=O)C)=NC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:28]([C:25]1[N:26]=[CH:27][C:22]([C:13]2[CH:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:9]3[S:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:11][C:10]=3[CH:12]=2)=[N:34][CH:33]=1)(=[O:31])[CH3:29]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 448286891-(5-Chloropyrazin-2-yl)ethan-1-oneHCID 71726538HCID 71726538, compound

Product 1

HCID 86696903HCID 86696903, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Intermediate 1 (171 mg, 0.5 mmol), 1-(5-chloropyrazin-2-yl)ethanone (94 mg, 0.60 mmol) and PdCl2(dppf) (41 mg, 0.05 mmol) were suspended in 1,4-dioxane (8 mL). A solution of Cs2CO3 (488 mg, 1.50 mmol) in H2O (2 mL) was added. The mixture was then heated under microwave irradiation at 100° C. for 30 min. The mixture was filtered, washed with H2O, EtOH, MeOH and Et2O to afford i (172 mg, 82%). MS: 419.06 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with H2O, EtOH, MeOH and Et2O
  3. customto afford i (172 mg, 82%)

Sources & evidence

ORD record
ord-a0bd37ef719e4936afecb897603b1757
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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