1-(p-Chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochloride → 1-(p Chlorobenzyl)-5-fluoro-3-methylthioindole-2-propanoic acid

HRID 483414Notes

Reaction equation

HRID 483414 reaction equation
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)N)=[CH:5][CH:4]=1.C[O:20][C:21](=[O:29])[CH2:22][CH2:23][C:24](=O)[CH2:25][S:26][CH3:27]>C(O)(C)(C)C>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:10]3[C:15](=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[C:25]([S:26][CH3:27])=[C:24]2[CH2:23][CH2:22][C:21]([OH:29])=[O:20])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 145912421-(p-Chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochlorideHCID 15035404Methyl 5-methylthio-4-oxopentanoate

Product 1

HCID 150353801-(p Chlorobenzyl)-5-fluoro-3-methylthioindole-2-propanoic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Following the procedure of Example 10, but using 1-(p-chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochloride and methyl-5-methylthio-4-oxopentanoate as starting materials and t-butanol as the solvent, the title compound was prepared. 1H NMR (250 MHz, CDCl3) δ 2.29 (s, 3H), 2.58 (broad t, 2H, J-7.8 Hz), 3.23 (broad t, 2H, J =7.8 Hz), 5.37 (s, 2H), 6.87 (d, 2H, J =8.5 Hz), 6.89-6.95 (m, 1H), 7.08 (dd, 1H, J =4.3 and 8.9 Hz), 7.25 (d, 2H, J =8.5 Hz), 7.40 (d,d, 1H, J =2.6 and 9.4 Hz).

Sources & evidence

ORD record
ord-6ede157f68e24ad2a765626f8c00a502
Source dataset
uspto-grants-1993_07
Patent number
US05225421

Reaction notes

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