Hydrochloric Acid → HCID 71059997, compound

HRID 405239Notes

Reaction equation

HRID 405239 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[C:17]2[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[O:24])=[N:21][CH:22]=2)=[CH:4][CH:3]=1.[C:33]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)(=[O:35])[CH3:34].C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:33]([C:36]1[CH:41]=[CH:40][C:39]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[C:17]3[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:24])=[N:21][CH:22]=3)=[CH:6][CH:7]=2)=[CH:38][CH:37]=1)(=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 71060047HCID 71060047, compound

Product 1

HCID 71059997HCID 71059997, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate (84 mg, 0.16 mmol), (4-acetylphenyl)boronic acid (32 mg, 0.20 mmol), Pd(dppf)Cl2 (18 mg, 0.02 mmol), 2M aqueous Na2CO3 (0.22 mL, 0.44 mmol) were dissolved in 1,4-dioxane (1.2 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, acidified with 2N HCl, filtered through CELITE and the filtrate was diluted with EtOAc, washed with water and saturated aqueous NaHCO3. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. temperatureAfter 16 h the resulting mixture was cooled to room temperature
  2. filtrationfiltered through CELITE
  3. additionthe filtrate was diluted with EtOAc
  4. washwashed with water and saturated aqueous NaHCO3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-9e05362acb2644f69ddf687fc1fb3bf4
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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