HCID 13732855, compound → HCID 20227232, compound

HRID 1731807Notes

Reaction equation

HRID 1731807 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]([N+:23]([O-])=O)[CH:19]=[CH:20][C:21]=2[F:22])[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=2[F:22])[NH2:23])[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 13732855HCID 13732855, compound

Product 1

HCID 20227232HCID 20227232, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 5.92 g 3-(3-t-butyldimethylsilyloxymethylphenyl)-4-fluoronitrobenzene in 200 ml 50% ethyl acetate/hexanes was hydrogenated over 5 g of 5% palladium on carbon at 50 p.s.i. for 15 minutes. The reaction mixture was filtered and evaporated to yield the crude product (5.43 g, 100% yield) which was used directly without further purification. On purification, the compound is characterized by the following data: NMR (CDCl3, 250 MHz): 7.45 (m, 4H), 6.98 (dd, 1H), 6.75 (dd, 1H), 6.62 (8 line multiplet, 1H), 4.8 (s, 2H), 3.6 (br s, 2H), 0.95 (s, 9H), 0.01 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-fc77fab023fb4b52a6dab556383c62a0
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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