Pyridine → HCID 54005039, compound

HRID 1954306Notes

Reaction equation

[C:1]([O:5][C:6](=[O:41])[C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([C:24]3[C:36]4[C:35]([CH3:37])=[C:34]([CH3:38])[S:33][C:32]=4[CH:31]=[C:30]4[C:25]=3[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:19][C:18]=2[CH3:39])(=[O:15])=[O:14])=[CH:9][C:8]=1[OH:40])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:48](Cl)(=[O:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>>[C:1]([O:5][C:6](=[O:41])[C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([C:24]3[C:36]4[C:35]([CH3:37])=[C:34]([CH3:38])[S:33][C:32]=4[CH:31]=[C:30]4[C:25]=3[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:19][C:18]=2[CH3:39])(=[O:14])=[O:15])=[CH:9][C:8]=1[O:40][C:48](=[O:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 1049Pyridine

HCID 7412Benzoyl chloride

HCID 54320327HCID 54320327, compound

Product 1

HCID 54005039HCID 54005039, compound

Procedure

The title compound was prepared according to the procedure in Example 17, step 1, using 4-[4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2, 6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid tert-butyl ester (0.072 g, 0.131 mmol), pyridine (63.4 μL, 0.784 mmol) and benzoyl chloride (30.5 μL, 0.262 mmol) to give a quantitative yield of the title compound. 1H NMR (DMSO-d6) δ 1.33 (s, 9 H), 1.57 (s, 3 H), 2.17 (s, 6 H), 2.31 (s, 3 H), 7.17 (s, 2 H), 7.36-7.48 (m, 3 H), 7.62-7.68 (m, 3 H), 7.78-7.82 (m, 1 H), 7.96 (t, 1 H), 8.10-8.24 (m, 4 H), 8.49 (s, 1 H).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-98a7935bcbeb481a99c0cc4c88d7ea1d
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121271

Reaction notes

Loading…