Trifluoroacetic acid → 2-(4-Aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole

HRID 2036719Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C(O)(C(F)(F)F)=O>>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17]2[CH2:23][CH:24]4[NH:28][CH:27]([C:16]3=2)[CH2:26][CH2:25]4)(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67085545Tert-butyl 2-(4-nitrophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 582588562-(4-Aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indoleYield 25%

Procedure

The product of step A was subjected to Boc-deprotection with TFA following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 1:9 methanol/dichloromethane) to give 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (25 mg, 25%) as a yellow oil: 1H NMR (CDCl3, 300 MHz) δ 8.16 (s, 1H), 7.49-7.65 (m, 4H), 6.62-6.67 (m, 2H), 5.24-5.25 (m, 1H), 4.51-4.53 (m, 1H), 3.68 (s, 3H), 3.34-3.50 (m, 1H), 2.97-3.05 (m, 1H), 2.34-2.45 (m, 2H), 2.20-2.27 (m, 1H), 1.96-1.98 (m, 1H).

Workup

customThe crude material was purified by flash column chromatography (SiO2, 1:9 methanol/dichloromethane)

Sources & evidence

ORD record: ord-917e94dd058042bcb51f743d1b2b1f28
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

Loading…