4,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indole → Ethyl 5-(aminomethyl)-2-chlorobenzoate

HRID 1846124Notes

Reaction equation

HRID 1846124 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9].CS[C:15]1C2C(=CC(Br)=CC=2Br)N[C:16]=1SC>Cl.CCO>[CH2:15]([O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:3]([CH2:2][NH2:1])[CH:4]=[CH:5][C:6]=1[Cl:12])[CH3:16]

Participants

5

Reactant 2

HCID 141858534,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indoleHCID 203783565-(Aminomethyl)-2-chlorobenzoic acid

Product 1

HCID 53418808Ethyl 5-(aminomethyl)-2-chlorobenzoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Prepared analogously to example 42d with 5-aminomethyl-2-chlorobenzoic acid (2 g; 9.01 mmol) in 20 mL HCl in EtOH. Yield: 2.38 g (90%); MS: [M+H]+=214 (Cl isotope pattern); HPLC: Rt=1.20 min (Method MC-6)

Sources & evidence

ORD record
ord-1e63a685749a4ab8af3293cb79f81ab2
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

Loading…