HCID 68704504, compound → HCID 68706330, compound

HRID 218159Notes

Reaction equation

HRID 218159 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:18][C:19]#[N:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H][H]>CO.Cl.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:18][CH2:19][NH2:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 68704504HCID 68704504, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68706330HCID 68706330, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

(c)(d) 3-(1-(4-Fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylonitrile (500 mg; 1.47 mmol) was dissolved in 20 mL MeOH and 4 mL 1 M HCl. 10% Pd on carbon (170 mg) was added and the reaction was hydrogenated in a Parr bottle over an atmosphere of 50 psi hydrogen for 16 h. The catalyst was filtered off and the solvent removed in vacuo to give pure 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropan-1-amine (492 mg, 100%) as a yellow oil. MS found: (M+H)+=376. 28 mg of this product (free base) was coupled to 2,2,2-trifluoroethanesulfonyl chloride using General Coupling Method B to give 20 mg (50%) of 2,2,2-trifluoro-N-(3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropyl)ethanesulfonamide. MS found: (M+H)+=492.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-88643637761a41a2a61e7f8a999934a3
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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