Vinyl chloroformate → vinyl 5-(3-bromo-4-fluorophenyl)-4,6-dioxo-4,5,6,7,9,10-hexahydro-1H-pyrano[3,4-b][1,7]naphthyridine-8(3H)-carboxylate

HRID 635979Notes

Reaction equation

HRID 635979 reaction equation
C([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[CH2:18][O:19][CH2:20][C:21](=[O:22])[C:13]=3[CH:12]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Br:30])[CH:24]=3)[C:11]=2[C:10](=[O:31])[CH2:9]1)C1C=CC=CC=1.Cl[C:33]([O:35][CH:36]=[CH2:37])=[O:34]>C(Cl)Cl>[Br:30][C:25]1[CH:24]=[C:23]([CH:12]2[C:11]3[C:10](=[O:31])[CH2:9][N:8]([C:33]([O:35][CH:36]=[CH2:37])=[O:34])[CH2:17][C:16]=3[NH:15][C:14]3[CH2:18][O:19][CH2:20][C:21](=[O:22])[C:13]2=3)[CH:28]=[CH:27][C:26]=1[F:29]

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 121240088-benzyl-5-(3-bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1H-pyrano[3,4-b][1,7]naphthyridine-4,6(3H,7H)-dione

Product 1

HCID 18000982vinyl 5-(3-bromo-4-fluorophenyl)-4,6-dioxo-4,5,6,7,9,10-hexahydro-1H-pyrano[3,4-b][1,7]naphthyridine-8(3H)-carboxylateYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 24A (0.29 g, 0.69 mmol) in methylene chloride (4 mL) was treated with vinyl chloroformate (0.10 mL, 1.2 mmol) and processed as in Example 2B. Purification by flash chromatography over silica gel (EtOAc) provided the title compound (0.13 g).

Workup

  1. customPurification by flash chromatography over silica gel (EtOAc)

Sources & evidence

ORD record
ord-e5356fcf443f4cafa8602c1591009691
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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