Hydrochloric Acid → HCID 71060073, compound

HRID 405231Notes

Reaction equation

HRID 405231 reaction equation
Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CC1(C)C(C)(C)OB([C:23]2[CH:24]=[CH:25][C:26]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:30])=[N:27][CH:28]=2)O1.C([O-])([O-])=O.[K+].[K+].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].O.CCOC(C)=O>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][CH2:32][NH:31][C:29]([C:26]1[N:27]=[CH:28][C:23]([C:2]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:24][CH:25]=1)=[O:30])[CH3:38]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 676052-Bromo-4-(trifluoromethyl)benzoic acidHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate

Product 1

HCID 71060073HCID 71060073, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-bromo-4-(trifluoromethyl)benzoic acid (538 mg, 2.0 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (1.0 g, 3.0 mmol), Pd(dppf)Cl2 (163 mg, 0.2 mmol), and K2CO3 (1.1 g, 8.0 mmol) were dissolved in 1,4-dioxane (12 mL) and water (4 mL) and heated to 90° C. After 3 h the resulting mixture was diluted EtOAc and water and 2N aqueous HCl was added until the pH of the aqueous layer was ca. 3-4. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated to yield the title compound, which was used in the next step without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fb8207f919204e38a7c980d7efdea2cc
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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