Sodium naphthalene-1-sulfinate → Tert-butyl 2-(1-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036709Notes

Reaction equation

HRID 2036709 reaction equation
[C:1]1([S:11]([O-:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Na+].Br[C:16]1[CH:24]=[CH:23][C:22]2[N:21]([CH3:25])[C:20]3[CH2:26][CH:27]4[NH:31][CH:30]([C:19]=3[C:18]=2[C:17]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]4>>[C:1]1([S:11]([C:16]2[CH:24]=[CH:23][C:22]3[N:21]([CH3:25])[C:20]4[CH2:26][CH:27]5[NH:31][CH:30]([C:19]=4[C:18]=3[C:17]=2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]5)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 23681220Sodium naphthalene-1-sulfinateHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085781Tert-butyl 2-(1-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 26%

Procedure

Intermediate 23 was coupled with the product of Example 27, step B following the procedure of Example 27, Step C. The crude product was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(1-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (120 mg, 26%) as a light yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.48 (dd, J=7.5, 1.2 Hz, 1H), 8.20 (s, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.86 (dd, J=8.6, 1.5 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 7.59 (t, J=7.8 Hz, 1H), 7.40-7.52 (m, 4H), 5.25 (br s, 1H), 4.69 (br s, 1H), 3.59 (s, 3H), 3.36 (br s, 1H), 2.45 (d, J=6.0 Hz, 1H), 2.14-2.38 (m, 2H), 1.87-1.96 (m, 1H), 1.59-1.67 (m, 1H), 1.37 (br s, 9H).

Workup

  1. customThe crude product was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d24f24f6212c41ed881fab5574626d28
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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