3-Bromobenzoic acid → HCID 20154392, compound

HRID 2413937Notes

Reaction equation

HRID 2413937 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[CH:17][CH:18]=2)[N:13]=1>O.CN(C)C=O.C(#N)C>[F:28][C:24]1[CH:23]=[C:22]([C:16]2[N:15]=[C:14]3[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:5](=[O:7])[C:4]4[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=4)=[N:13]3)=[CH:18][CH:17]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 114563-Bromobenzoic acidHCID 13983425HCID 13983425, compound

Product 1

HCID 20154392HCID 20154392, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 11, but starting with 3-bromobenzoic acid (2.8 g), N,N'-carbonyldiimidazole (2.3 g) and 2-amino-7-(3-fluorophenyl)-1,8-naphthyridine (2.4 g). The product obtained by precipitation in water (3.5 g; m.p. approximately 195° C.) is dissolved in a boiling mixture of dimethylformamide (20 cc) and acetonitrile (200 cc). After cooling for 4 hours at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (3×10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-[7-(3-Fluorophenyl)-1,8-naphthyridin-2-yl]-3-bromobenzamide (2.3 g), m.p. 208° C., is obtained.

Workup

  1. customthe crystallized solid is separated by filtration
  2. washwashed with acetonitrile (3×10 cc)
  3. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-8d03c66fb19d4f7ab0f058b32b9732b4
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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