Potassium Carbonate → HCID 86634338, compound

HRID 425971Notes

Reaction equation

HRID 425971 reaction equation
Br[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:4]([C:24]#[N:25])[CH:3]=1.[CH3:26]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:8][C:7]1[C:2]([CH3:26])=[CH:3][C:4]([C:24]#[N:25])=[C:5]([NH:9][C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 86634339HCID 86634339, compound

Product 1

HCID 86634338HCID 86634338, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

tert-Butyl {(1S,2S)-2-[(4-bromo-5-chloro-2-cyanophenyl)amino]cyclohexyl}carbamate, trimethyl boroxine and potassium carbonate were suspended in a mixed solvent of 1,4-dioxane (16 ml) and water (4 ml), tetrakis(triphenylphosphine)palladium was added thereto, followed by stirring at 110° C. for 1 day. By post-treating the reaction liquid, tert-butyl {(1S,2S)-2-[(5-chloro-2-cyano-4-methylphenyl)amino]cyclohexyl}carbamate was obtained.

Workup

  1. additionwas added
  2. additionBy post-treating
  3. customthe reaction liquid

Sources & evidence

ORD record
ord-478c3bde151a49999fd4ca85986a7372
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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