Oxalyl chloride → HCID 59737512, compound

HRID 1907759Notes

Reaction equation

HRID 1907759 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.[C:13](Cl)(=O)[C:14](Cl)=O.Br[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([N+:34]([O-])=O)[CH:21]=1>C(Cl)Cl.CN(C=O)C.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:34][C:22]1[CH:21]=[C:20]([C:14]2[CH:13]=[CH:27][N:26]=[CH:23][CH:22]=2)[CH:25]=[CH:24][C:23]=1[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:7]

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 27334013-Fluoro-4-methoxybenzoic acidHCID 52904808tert-Butyl (4-bromo-2-nitrophenyl)carbamate

Product 1

HCID 59737512HCID 59737512, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-fluoro-4-methoxybenzoic acid (125 mg, 0.736 mmol) in DCM (10 mL), oxalyl chloride (0.442 mL, 0.883 mmol) and DMF (2 drops) were added. The reaction was stirred at room temperature for 30 min and a solution was obtained. A solution of compound 390 (210 mg, 0.736 mmol) (390 was synthesized following general procedures B and C starting from compound 2 and pyridin-4-ylboronic acid) in pyridine (10 mL) was added and the reaction was stirred for an additional hour, quenched with water, dissolved in AcOEt and washed with water. The organic layer was separated and dried with Na2SO4, filtered and concentrated under vacuum. The residue was purified via Isco (12 g column, 40-100% EtOAc/hexanes solvent gradient) to give the title compound 391 as a light yellowed (60 mg, 18% yield).

Workup

  1. additionwere added
  2. customa solution was obtained
  3. stirringthe reaction was stirred for an additional hour
  4. customquenched with water
  5. dissolutiondissolved in AcOEt
  6. washwashed with water
  7. customThe organic layer was separated
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe residue was purified via Isco (12 g column, 40-100% EtOAc/hexanes solvent gradient)

Sources & evidence

ORD record
ord-eb1cbc37f1514cb68fcc7c14ec6e3e56
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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