3-Bromo-4-fluorobenzaldehyde → 5-(3-bromo-4-fluorophenyl)-3,3-dimethyl-5,7,8,9-tetrahydrocyclopenta[b]pyrano[4,3-e]pyridine-4,6(1H,3H)-dione

HRID 478307Notes

Reaction equation

HRID 478307 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[CH3:18][C:19]1([CH3:27])[C:24](=[O:25])[CH2:23][C:22](=O)[CH2:21][O:20]1>>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]2[C:23]3[C:24](=[O:25])[C:19]([CH3:27])([CH3:18])[O:20][CH2:21][C:22]=3[NH:1][C:2]3[CH2:6][CH2:5][C:4](=[O:7])[C:3]2=3)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

4

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 122914403-Aminocyclopent-2-en-1-oneHCID 140728872,2-dimethyl-2H-pyran-3,5(4H,6H)-dione

Product 1

HCID 180009995-(3-bromo-4-fluorophenyl)-3,3-dimethyl-5,7,8,9-tetrahydrocyclopenta[b]pyrano[4,3-e]pyridine-4,6(1H,3H)-dioneYield 54.2%

Procedure

3-Amino-2-cyclopenten-1-one (Kikani, B. B., Synthesis, (1991), 2,176) (0.099 g, 1.0 mmol), 3-bromo-4-fluorobenzaldehyde (0.21 g, 1.0 mmol) and the product from Example 66C (0.15 g, 1.0 mmol) were processed as described in Example 31 to provide the title compound (0.22 g).

Sources & evidence

ORD record
ord-370d177f7f74469e8fb32fe5a43babdb
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

Loading…