2-Bromoaniline → 1-[2-(4-Methylthiophenyl)phenyl]piperidine

HRID 233574

Reaction equation

HRID 233574 reaction equation
Br[C:2]1[CH:8]=[CH:7]C=[CH:5][C:3]=1N.[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[NH2:19])=[CH:13][CH:12]=1.BrC(Br)(CC)CC>C(N(CC)CC)C>[CH3:9][S:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]2[CH2:7][CH2:8][CH2:2][CH2:3][CH2:5]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 119922-Bromoaniline2×HCID 27600692-[4-(Methylsulfanyl)phenyl]anilineHCID 135557303,3-Dibromopentane

Product 1

HCID 543694301-[2-(4-Methylthiophenyl)phenyl]piperidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Compounds of Formula I wherein X is a single bond and R1 is 1-piperidinyl or 1-pyrrolyl can be prepared from 2-bromoaniline as shown in Scheme 15. Suzuki coupling of 2-bromoaniline with 4-thiomethylphenylboronic acid using the method described above followed by condensation of the resulting 2-(4-methylthiophenyl)aniline with dibromopentane in the presence of an amine base, such as triethylamine, affords the corresponding 1-[2-(4-methylthiophenyl)phenyl]piperidine. Oxidation if the methylthio to the methylsulfonyl using methods described above provides compounds of Formula I wherein R1 is 1-piperidinyl. Alternately the starting 2-bromoaniline can be converted to the 1-[(2-bromophenyl)phenyl]pyrrole by treatment with 2,5-dimethoxytetrahydrofuran in glacial acetic acid. Suzuki coupling of the resulting intermediate with 4-methylthiophenylboronic acid followed by oxidation, as described above, gives the 1-[2-(4-methylsulfonylphenyl)phenyl]pyrrole. ##STR26##

Sources & evidence

ORD record
ord-67cce953bb674678b39c794817cc2e3c
Source dataset
uspto-grants-1997_01
Patent number
US05593994

Linked notes

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