Water → 6-(4-Carboxyphenyl)-8-(4-benzo[c]furazanyl)-1,7-naphthyridine

HRID 369036Notes

Reaction equation

HRID 369036 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18](OC)[N:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([OH:3])=[O:2].P(Br)(Br)Br.[OH2:26].C[N:28]([CH:30]=O)C>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([C:11]4[C:30]5[C:15](=[N:16][O:26][N:28]=5)[CH:14]=[CH:13][CH:12]=4)[N:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24614Phosphorus tribromideHCID 232846426-(4-Carboxyphenyl)-8-methoxy-1,7-naphthyridine

Product 1

HCID 232846386-(4-Carboxyphenyl)-8-(4-benzo[c]furazanyl)-1,7-naphthyridine

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(4-carboxyphenyl)-8-methoxy-1,7-naphthyridine (250 mg, 0.892 mmol) in DMF (10 ml) is added PBr3 (0.63 ml, 6.63 mmol). The reaction mixture is heated to 100° C. for 30 min. Then, the suspension is poured into water (50 ml) and the solution washed with ethyl acetate (2×50 ml). The organic solvent is removed and the crude product stirred in ether. The suspension is filtered to yield the title compound (215 mg). Melting point 248-250, decomposition.

Workup

  1. washthe solution washed with ethyl acetate (2×50 ml)
  2. customThe organic solvent is removed
  3. filtrationThe suspension is filtered

Sources & evidence

ORD record
ord-7383140af9984851b4664015929823d8
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Reaction notes

Loading…