(S)-1-(4-Fluorophenyl)-ethylamine → (S)-5,6-difluoro-N-(1-(4-fluorophenyl)ethyl)-3-nitropyridin-2-amine

HRID 1437437Notes

Reaction equation

HRID 1437437 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4](F)[N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=1>C1COCC1>[F:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]([NH:22][C@H:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH3:21])=[N:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 674554212,3,6-Trifluoro-5-nitropyridine

Product 1

HCID 67452698(S)-5,6-difluoro-N-(1-(4-fluorophenyl)ethyl)-3-nitropyridin-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,3,6-trifluoro-5-nitropyridine (Method 56, 2.0 g, 11.2 mmol) in THF (50 ml) was cooled to 0° C., to which was added (S)-1-(4-fluorophenyl)ethanamine (1.56 g, 11.2 mmol). The reaction was stirred at 0° C. for 30 min., then quenched with water (50 ml) and extracted with DCM (2×75 ml). The combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (hexanes-DCM=1:1) to give the title compound (2.3 g, 70%).

Workup

  1. customquenched with water (50 ml)
  2. extractionextracted with DCM (2×75 ml)
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by column chromatography (hexanes-DCM=1:1)

Sources & evidence

ORD record
ord-257b058d27e54e6bb92f0dc1413fa272
Source dataset
uspto-grants-2009_11
Patent number
US07622482B2

Reaction notes

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