HCID 66842110, compound → HCID 66842123, compound

HRID 1158837Notes

Reaction equation

HRID 1158837 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N+:31]([O-:33])=[O:32])=[CH:13][N:14]2[CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:10][CH:9]=1)(C)(C)C>CCCCCCC.C(OCC)(=O)C.C(O)C>[N+:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[S:24][C:12]1[C:11]2[C:15](=[CH:16][C:8]([NH2:7])=[CH:9][CH:10]=2)[N:14]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:13]=1)([O-:33])=[O:32]

Participants

3

Reactant 1

HCID 66842110HCID 66842110, compound

Product 1

HCID 66842123HCID 66842123, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 86615354HCID 86615354, compoundSolvent

Procedure

[3-(2-Nitro-phenylsulfanyl)-1-pyridin-3-ylmethyl-1H-indol-6-yl]-carbamic acid tert-butyl ester (Example 3, step iv; 5.96 g, 12.5 mmol) was deprotected to give, after column chromatography (heptane/ethyl acetate/ethanol 4:4:1), the title compound (1.50 g). 1H-NMR (CDCl3) δ 8.55-8.60 (m, 2H), 8.26 (dd, 1H, J=8.5 and 1.5 Hz), 7.42 (dt, 1H, J=8.0 and 1.5 Hz), 7.24-7.33 (m, 3H), 7.17 (ddd, 1H, J=8.0, 7.0 and 1.0 Hz), 7.01 (dd, 1H, J=8.0 and 1.5 Hz), 6.60 (m, 2H), 6.59 (s, 1H), 5.30 (s, 2H).

Workup

  1. customto give

Sources & evidence

ORD record
ord-54cdea70dab34f638aabed459792ab89
Source dataset
uspto-grants-2010_10
Patent number
US07812036B2

Reaction notes

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