Cesium carbonate → HCID 86652626, compound

HRID 1921739Notes

Reaction equation

HRID 1921739 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])(=[O:21])=[O:20])=[CH:15][CH:14]=1.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]>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])(=[O:20])=[O:21])=[CH:15][CH:14]=2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 121268HCID 121268, compoundHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 86652626HCID 86652626, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

A mixture of 5,8-dibromoimidazo[1,2-a]pyrazine (1.0 g, 3.6 mmol), 4-amino-N-(2-diethylaminoethyl)benzenesulfonamide (109 mg, 0.4 mmol), Pd2(dba)3 (7 mg, 0.007 mmol), Xantphos (8.4 mg, 0.015 mmol) and Cs2CO3 (167 mg, 0.52 mmol) in dioxane is heated at 85° C. under nitrogen for 18 hours. The reaction is cooled to room temperature then evaporated to dryness. The residue is chromatographed on silica gel, eluting with DCM then 98:2 DCM:NH3 (7N in MeOH), and the fractions containing the title compound are combined and evaporated to afford a dark oil. This oil contains an impurity, but is used in the subsequent step without further purification.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. customthen evaporated to dryness
  3. customThe residue is chromatographed on silica gel
  4. washeluting with DCM
  5. addition98:2 DCM:NH3 (7N in MeOH), and the fractions containing the title compound
  6. customevaporated
  7. customto afford a dark oil
  8. customis used in the subsequent step without further purification

Sources & evidence

ORD record
ord-461fb07118454eda9e2e47cd3a5caf9b
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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