Boron Trichloride → 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylic acid

HRID 1058681Notes

Reaction equation

HRID 1058681 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([O:17]C)=[O:16])=[C:13]([CH3:19])[NH:12][C:11]3[CH2:20][CH2:21][C:22](=[O:23])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].B(Cl)(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]3[CH2:20][CH2:21][C:22](=[O:23])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 11383413methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate

Product 1

HCID 98639534-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylic acidYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of the product from Example 10A (1.90 g, 5.0 mmol) in methylene chloride (10 mL) at 5° C. under nitrogen was treated with 1M boron trichloride in methylene chloride (40 mL), stirred overnight, quenched in ice water (100 mL) and ethyl acetate (30 mL), and the aqueous drained off. The suspension of the product in ethyl acetate was filtered, the filter cake was washed with ethyl acetate and dried to provide 1.26 g of the title compound as an orange-pink solid.

Workup

  1. customquenched in ice water (100 mL)
  2. additionThe suspension of the product in ethyl acetate
  3. filtrationwas filtered
  4. washthe filter cake was washed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-866e2239ebd042219c80577e39461d63
Source dataset
uspto-grants-2003_02
Patent number
US06518279B2

Reaction notes

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