Potassium Phosphate, Tribasic → HCID 58065892, compound

HRID 1028297Notes

Reaction equation

HRID 1028297 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:50]2[CH2:55][CH2:54]CCC2)C2CCCCC2)CCCCC1>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:23]1([C:10]2[CH:9]=[CH:8][C:7]3[N:6]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:5]4[C:13]([C:12]=3[CH:11]=2)=[CH:14][C:2]([CH:54]2[CH2:55][CH2:50]2)=[CH:3][CH:4]=4)[CH2:25][CH2:24]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 58065882HCID 58065882, compound

Product 1

HCID 58065892HCID 58065892, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Following a literature procedure (Petit et al., ChemMedChem 2009, 4, 261-275.), tert-butyl 3,6-dibromo-9H-carbazole-9-carboxylate (0.0200 g, 0.0470 mmol), cyclopropyl boronic acid (0.0202 g, 0.235 mmol), palladium acetate (10 mol %, 0.0011 g, 0.00470 mmol), potassium phosphate tribasic (0.0350 g, 0.165 mmol), tricyclohexylphosphine (0.0026 g, 0.00941 mmol), water (12.2 μL) and a stir bar were combined in a sealed vial. The vial was sparged with N2 and charged with 0.22 mL degassed toluene. The mixture was stirred at 100° C. for 65 h. The crude reaction mixture was diluted with 10 mL EtOAc and washed with brine (3×10 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was used as is without further purification.

Workup

  1. customThe vial was sparged with N2
  2. additioncharged with 0.22 mL
  3. customdegassed toluene
  4. customThe crude reaction mixture
  5. washwashed with brine (3×10 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-1f09fed7399446689f1262d4798be5f6
Source dataset
uspto-grants-2014_05
Patent number
US08735440B2

Reaction notes

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