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N-methyl-2-pyrrolidone → 5-Aminomethyl-N-tert-butyl-2-fluoro-benzenesulfonamide

HRID 42342
Notes
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Reaction equation

HRID 42342 reaction equation
NCC1C=CC(S([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=O)=O)=CC=1C.Cl[C:19]1[CH:20]=[CH:21][C:22]([F:29])=[C:23]([S:25](Cl)(=[O:27])=[O:26])[CH:24]=1.[CH3:30][N:31]1C(=O)CCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:31][CH2:30][C:19]1[CH:20]=[CH:21][C:22]([F:29])=[C:23]([S:25]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:27])=[O:26])[CH:24]=1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 27782735-Chloro-2-fluorobenzenesulfonyl chlorideHCID 582753444-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide

Product 1

HCID 287163695-Aminomethyl-N-tert-butyl-2-fluoro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst

Conditions

Temperature
120 °C

Procedure

5-Aminomethyl-N-tert-butyl-2-fluoro-benzenesulfonamide was synthesized in a manner analogous to 4-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide in Example 4, using 5-chloro-2-fluorobenzene-1-sulfonyl chloride in place of 4-bromo-3-methylbenzene-1-sulfonyl chloride. In the second step NMP was used as the solvent, Pd(dppf)Cl2 alone was used as catalyst and the reaction mixture was stirred at 120° C. for 15 hours.

Sources & evidence

ORD record
ord-d091dfa4a41044699fc0cce15c88e16a
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536187B2

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes