Benzamide → HCID 58514094, compound

HRID 1910735Notes

Reaction equation

HRID 1910735 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[C:17]([NH2:25])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:14]([C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:25][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=1)(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 2331BenzamideHCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2×HCID 58514136HCID 58514136, compound

Product 1

HCID 58514094HCID 58514094, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

A degassed mixture of 1-[3-(2-Chloro-pyridin-4-yl)-phenyl]-ethanone (500 mg, 2.16 mmol), benzamide (523 mg, 4.32 mmol, 2 eq.), Xantphos (120 mg, 0.21 mmol, 0.1 eq.), Pd(OAc)2 (24 mg, 0.10 mmol, 0.05 eq.), K2CO3 (448 mg, 3.24 mmol, 1.5 eq.) in dioxane (12 mL) was irradiated with microwaves at 150° C. for 1 hour. LC/MS control. Conversion was mostly 100% based on disappearance of starting material. Dimer (M+: 392) being the major by-product. If any starting material is unreacted at this point, another portion of Xantphos and Pd(OAc)2 may be added and the mixture microwaved for another 30 minutes. The mixture was then partitioned between DCM and water (20 mL/10 mL). The layers were separated and the aqueous layer was washed further with DCM (2×20 mL). The combined organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was chromatographed using 1/1 Hexane/EtOAc to give N-[4-(3-Acetyl-phenyl)-pyridin-2-yl]-benzamide as a white solid (375 mg, 55%). MS: m/z 317.1 [MH+].

Workup

  1. customwas irradiated with microwaves at 150° C. for 1 hour
  2. customthe mixture microwaved for another 30 minutes
  3. customThe mixture was then partitioned between DCM and water (20 mL/10 mL)
  4. customThe layers were separated
  5. washthe aqueous layer was washed further with DCM (2×20 mL)
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was chromatographed

Sources & evidence

ORD record
ord-8932106e21c44cc1bd0f117426fa33a0
Source dataset
uspto-grants-2013_12
Patent number
US08604031B2

Reaction notes

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