3-Chloro-4-fluoroaniline → HCID 22390975, compound

HRID 397398Notes

Reaction equation

HRID 397398 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:11][C:12]1[CH:13]=[C:14]([NH2:19])[CH:15]=[CH:16][C:17]=1[F:18]>CN(C=O)C.C(OCC)(=O)C.FC(F)(F)S([O-])(=O)=O.[Ag+]>[Cl:11][C:12]1[CH:13]=[C:14]([NH:19][C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

6

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 22390975HCID 22390975, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (767.9 mg, 5 mmol) and 3-chloro-4-fluoro-phenylamine (873.4 mg, 6 mmol) in 25 mL of dry DMF under nitrogen was added silver trifluoromethanesulfonate (1.54 g, 6 mmol). The mixture was stirred at 95° C. for 15 hours. The cooled reaction was diluted with ethyl acetate (70 mL) and filtered through celite, washed thoroughly with ethyl acetate. The filtrate was washed with brine (5×). The brine was extracted with ethyl acetate which was then washed with brine. The combined ethyl acetate was dried (magnesium sulfate), concentrated and purified to give 1.22 g (93%) of (3-chloro-4-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine as an off-white solid. m.p. 274-275 ° C. 1H NMR (360 MHz, DMSO-d6) δ 11.78 (br s, 1H, NH), 9.41 (s, 1H), 8.31 (s, 1H), 8.28 (m, 1H), 7.79 (m, 1H), 7.37 (t, 1H), 7.25 (m, 1H), 6.76 (m, 1H). MS 263.4 [M+].

Workup

  1. customThe cooled reaction
  2. filtrationfiltered through celite
  3. washwashed thoroughly with ethyl acetate
  4. washThe filtrate was washed with brine (5×)
  5. extractionThe brine was extracted with ethyl acetate which
  6. washwas then washed with brine
  7. dry with materialThe combined ethyl acetate was dried (magnesium sulfate)
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-78e7b63a994947379e1c01cf7a9ce2ff
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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