C16H22F6IN2P → 1-Benzyl-8-hydroxy-5-iodo-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

HRID 919795Notes

Reaction equation

HRID 919795 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][N:6]=1)=[O:4].CC1C=C(C)N=C(C)C=1.CC1C([IH+:40])=C(C)N=C(C)C=1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:7]([I:40])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 46863890C16H22F6IN2PHCID 682971941-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

Product 1

HCID 867141181-Benzyl-8-hydroxy-5-iodo-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl esterYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester (200 mg, 0.645 mmol) and bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate (0.83 g, 1.61 mmol) in 10 mL of CH2Cl2 was stirred at r.t. for 16 h. The mixture was diluted with CH2Cl2 and washed with dilute NaHSO3 and 1 M HCl. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (100% CH2Cl2) to give 113 mg of the title compound as a pale yellow solid. MS: (+) m/z 437.13 (M+1).

Workup

  1. washwashed with dilute NaHSO3 and 1 M HCl
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (100% CH2Cl2)

Sources & evidence

ORD record
ord-0c7ffbc5f5384c0991f32bf401a5d215
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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