Ethyl Acetate → HCID 66842051, compound

HRID 1158836Notes

Reaction equation

HRID 1158836 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:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:10][CH:9]=1)(C)(C)C.CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>C(N(CC)CC)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:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:13]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21899848Ethylacetate heptaneHCID 66842045HCID 66842045, compound

Product 1

HCID 66842051HCID 66842051, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

[3-(2-Nitro-phenylsulfanyl)-1-pyridin-2-ylmethyl-1H-indol-6-yl]-carbamic acid tert-butyl ester (Example 2, step iv; 3.4 g, 6.3 mmol) was deprotected to give, after column chromatography (heptane/ethyl acetate 2:8→ethyl acetate, containing some triethylamine), the title compound (1.54 g). 1H-NMR (CDCl3) δ 8.62 (bd, 1H, J=5.0 Hz), 8.26 (dd, 1, J=8.0 and 1.5 Hz), 7.61 (dt, H, J=7.5 and 2.0 Hz), 7.34 (s, 1H), 7.25-7.30 (m, 2H), 7.22 (ddd, 1H, J=7.5, 5.0 and 1.0 Hz), 7.16 (ddd, 1H J=8.0, 7.0 and 1.0 Hz), 7.05 (dd, 1H, J=8.0 and 1.0 Hz), 6.86 (d, 1H, J=8.0 Hz), 6.63 (d, 1H, J=1.5 Hz), 6.60 (dd, 1H, J=8.0 and 1.5 Hz), 5.41 (s, 2H), 3.70 (bs, 2H).

Workup

  1. customto give

Sources & evidence

ORD record
ord-5598448020c945708bd879e9d8ae1b17
Source dataset
uspto-grants-2010_10
Patent number
US07812036B2

Reaction notes

Loading…