Potassium Carbonate → HCID 67958044, compound

HRID 919040Notes

Reaction equation

HRID 919040 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1Br)[CH3:9].[OH:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[C:25]1[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=1)[CH3:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 67957737HCID 67957737, compound

Product 1

HCID 67958044HCID 67958044, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

(3-Bromo-pyridin-4-yl)-carbamic acid 1-(2-chloro-phenyl)-ethyl ester (0.180 g, 0.51 mmol), 4-hydroxyphenylboronic acid (0.104 g, 0.76 mmol) and potassium carbonate (0.245 g, 1.78 mmol) were suspended in DME:H2O (2:1, 3 mL). The suspension was purged with N2 (g) for 5 minutes then tetrakis(triphenylphosphine)palladium(0) (0.058 g, 0.051 mmol) was added and the N2 (g) purge continued for 5 additional minutes. The reaction vessel was sealed and heated to 80° C. for 1 hour then allowed to cool. The reaction mixture was submitted to EtOAc/H2O workup then purified on silica gel to yield the title compound.

Workup

  1. customThe suspension was purged with N2 (g) for 5 minutes
  2. customthe N2 (g) purge
  3. customThe reaction vessel was sealed
  4. temperatureto cool
  5. customthen purified on silica gel

Sources & evidence

ORD record
ord-0bea5022ecb94a19ab63639d1ab45430
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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