Trifluoroacetic acid → HCID 57401298, compound

HRID 2036714Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67085117HCID 67085117, compound

Product 1

HCID 57401298HCID 57401298, compoundYield 26%

Procedure

The product of step A was subjected to Boc-deprotection with TFA following the procedure of Example 28, Step B. The crude product was purified by flash column chromatography (SiO2, 1:9 methanol/dichloromethane) to give 2-(4-chlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (20 mg, 26%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ 8.12-8.14 (m, 1H), 7.83-7.94 (m, 2H), 7.61 (d, J=7.8 Hz, 1H), 7.51-7.55 (m, 2H), 7.45-7.48 (m, 1H), 4.59 (d, J=2.7 Hz, 1H), 4.01-4.05 (m, 1H), 3.64 (s, 3H), 3.16-3.23 (m, 1H), 2.61-2.67 (m, 1H), 1.94-2.23 (m, 3H), 1.59-1.67 (m, 1H).

Workup

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

Sources & evidence

ORD record: ord-80aae79703cc41d88ccfa46faf68d8d2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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