4,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indole → 3-Aminomethyl-2-chloro-6-methylbenzoic acid 3-aminomethyl-2-methyl-6-chlorobenzoic acid

HRID 1846112Notes

Reaction equation

HRID 1846112 reaction equation
[Cl:1][C:2]1[C:10]([CH2:11][NH:12]C(C(F)(F)F)=O)=[C:9](F)[C:8](F)=[C:7]([CH3:21])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:22][C:23]1[C:31]([CH2:32][NH:33]C(C(F)(F)F)=O)=[C:30](F)[C:29](F)=[C:28]([Cl:42])[C:24]=1[C:25]([OH:27])=[O:26].CSC1C2C(=CC(Br)=CC=2Br)NC=1SC>Cl>[NH2:12][CH2:11][C:10]1[C:2]([Cl:1])=[C:3]([C:7]([CH3:21])=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5].[NH2:33][CH2:32][C:31]1[C:23]([CH3:22])=[C:24]([C:28]([Cl:42])=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 141858534,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indoleHCID 1317324292-Chloro-6-methyl-difluoro-3-(trifluormethylcarbonylamino)methyl-benzoic acid 2-methyl-6-chloro-difluoro-3-(trifluormethylcarbonylamino)methyl-benzoic acid

Product 1

HCID 866586753-Aminomethyl-2-chloro-6-methylbenzoic acid 3-aminomethyl-2-methyl-6-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Prepared analogously to 44a with 2-chloro-6-methyl-difluoro-3-(trifluormethylcarbonylamino)methyl-benzoic acid/2-methyl-6-chloro-difluoro-3-(trifluormethylcarbonylamino)methyl-benzoic acid (5.62 g 19 mmol) in 6 M aq. HCl solution. Yield: 4.37 g; (97%; mixture of regioisomers); MS: [M−H]−=198; HPLC: Rt=0.189 min (Method MC-6)

Workup

  1. addition(97%; mixture of regioisomers)

Sources & evidence

ORD record
ord-848499b27b61419996e23dabe45582ff
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

Loading…