Cesium carbonate → HCID 86683727, compound

HRID 519320Notes

Reaction equation

HRID 519320 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][O:9][CH2:10][CH:3]1[CH2:4][N:5]([C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=1)[CH2:6]2.Br[C:19]1[C:20](=[O:27])[N:21]([CH3:26])[CH:22]=[C:23]([Br:25])[CH:24]=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:25][C:23]1[CH:24]=[C:19]([NH:17][C:14]2[CH:13]=[CH:12][C:11]([N:5]3[CH2:6][CH:7]4[N:2]([CH3:1])[CH:3]([CH2:10][O:9][CH2:8]4)[CH2:4]3)=[CH:16][N:15]=2)[C:20](=[O:27])[N:21]([CH3:26])[CH:22]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 86683726HCID 86683726, compound

Product 1

HCID 86683727HCID 86683727, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
105 °C

Procedure

To a solution of 112j (500 mg, 2.1 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (852 mg, 3.2 mmol) in dioxane (100 ml) was added Xantphos (58 mg, 0.1 mmol), Cs2CO3 (2.1g, 6.4 mmol) and Pd2(dba)3 (110 mg, 0.1 mmol). The reaction mixture was stirred at 105° C. overnight. The mixture was cooled to RT, filtered, concentrated, and the crude product was purified through a silica gel column eluting with MeOH:DCM=0 to 1:5 to 112k (500 mg, 46.4%). MS: [M+H]+: 421

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customthe crude product was purified through a silica gel column
  5. washeluting with MeOH

Sources & evidence

ORD record
ord-008e3ae9e3144de28f865396b12f0f80
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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