Acetic Acid → HCID 57585899, compound

HRID 547653Notes

Reaction equation

HRID 547653 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=2)[C:9]([F:21])=[CH:8][C:7]=1[N+:22]([O-:24])=[O:23])=O.[NH2:27][CH:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[NH2:5][C:6]1[C:7]([N+:22]([O-:24])=[O:23])=[CH:8][C:9]([F:21])=[C:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][NH:27][CH:28]3[CH2:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29]3)=[CH:17][CH:18]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 763102-AminoindaneHCID 5049666Sodium triacetoxyborohydrideHCID 57585870HCID 57585870, compound

Product 1

HCID 57585899HCID 57585899, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2,2-trifluoro-N-{4-fluoro-5-[(4-formylphenyl)oxy]-2-nitrophenyl}acetamide (0.300 g, 0.806 mmol), 2-aminoindane (0.161 g, 1.21 mmol), and acetic acid (0.5 mL) in CH2Cl2 (3 mL) was stirred for 30 min and then Na(OAc)3BH (0.205 g, 0.967 mmol) was added slowly over 2 min. The reaction mixture stirred for 1 hour at ambient temperature and then H2O (3 mL) was added. The layers were separated and the aqueous layer extracted one additional time with CH2Cl2. The combined organics were washed 1× brine, then dried (Na2SO4), filtered and concentrated to give ({4-[(5-Amino-2-fluoro-4-nitrophenyl)oxy]phenyl}methyl)2,3-dihydro-1H-inden-2-ylamine. No further purification was necessary.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted one additional time with CH2Cl2
  3. washThe combined organics were washed 1× brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3195870fccf14d99ab6946faf89f79ac
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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