180058-71-3

Basic information

• Product Name: 2,6-Dibromo-4-methylaminosulfonylmethylaniline
• Synonyms: 2,6-Dibromo-4-methylaminosulfonylmethylaniline
• CAS NO: 180058-71-3
• Molecular Weight: 358.054
• Mol File: 180058-71-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,6-Dibromo-4-methylaminosulfonylmethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dibromo-4-methylaminosulfonylmethylaniline(180058-71-3)
• EPA Substance Registry System: 2,6-Dibromo-4-methylaminosulfonylmethylaniline(180058-71-3)

Safety Data

• Hazardous Substances Data: 180058-71-3(Hazardous Substances Data)

Upstream product

• 109903-35-7 1-(4-aminophenyl)-N-methylmethanesulfonamide 

Downstream Products

• 180058-72-4 2,6-Dibromo-4-methylaminosulfonylmethyl-N-trifluoroacetylaniline 
• 180058-75-7 (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-7-bromo-5-(methylaminosulfonylmethyl)-1H-indole 

Relevant articles and documents

An improved synthesis of the unique anti-migraine agent CP-122,288: A bromine atom passenger in an intramolecular Heck reaction

Utilizing a 2,6-dibromoaniline (6b) in place of the original monobromo aniline in the indole-forming intramolecular Heck reaction allows for a greater than two-fold improvement in the overall yield of CP-122,288. The second bromine is carried through unmolested, forming a 7-bromoindole analog of CP-122,288 (1b). This result might represent a novel approach to 7- substituted indole derivatives.

INDOLE DERIVATIVES

Compounds of the formula STR1 wherein n is 0, 1, or 2; X is hydrogen, chlorine, bromine or iodine; R 1 is hydrogen; R 3 is selected from hydrogen and C 1 to C 6 linear or branched alkyl; and R 2 is as defined in the specification and the pharmaceutically acceptable salts thereof are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of a dihalogenated intermediate is also disclosed.

INDOLE DERIVATIVES

Compounds of the formula STR1 wherein R 1, R 2, R. sub.3, X and n are as defined in the claims and the pharmaceutically acceptable salts thereof are new. These compounds are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting hypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of dihalogenated intermediate is also disclosed.