Nicotinic Acid → HCID 23295996, compound

HRID 1954309Notes

Reaction equation

C([O:5][C:6](=[O:42])[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[C:31]([Br:39])=[C:30]4[C:25]=3[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:19][C:18]=2[CH3:40])(=[O:15])=[O:14])=[CH:9][C:8]=1[OH:41])(C)(C)C.[C:43](O)(=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[N:46][CH:45]=1.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>>[C:6]([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[C:31]([Br:39])=[C:30]4[C:25]=3[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:19][C:18]=2[CH3:40])(=[O:15])=[O:14])=[CH:9][C:8]=1[O:41][C:43](=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[N:46][CH:45]=1)([OH:5])=[O:42]

Participants

Reactant 4

HCID 938Nicotinic Acid

HCID 8471Triethylamine

HCID 1670692-Chloro-1-methylpyridinium iodide

HCID 9896063HCID 9896063, compound

Product 1

HCID 23295996HCID 23295996, compoundYield 80%

Procedure

The title compound was prepared according to the procedure in Example 25, step 1, using 4-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid tert-butyl ester (0.500 g, 0.749 mmol), nicotinic acid (0.092 g, 0.749 mmol), 2-chloro-1-methylpyridinium iodide (0.230 g, 0.899 mmol) and triethylamine (0.251 mL, 1.80 mmol). Purification on Biotage KP-Sil eluting with 20% EtOAc/hexane gave 0.460 g, (80%) of the title compound. 1H NMR (DMSO-d6) 6 1.34 (s, 9 H), 1.55 (s, 3 H), 2.16 (s, 6 H), 2.36 (s, 3 H), 7.19 (s, 2 H), 7.45-7.46 (m, 2 H), 7.61-7.71 (m, 2 H), 8.12-8.25 (m, 4 H), 8.50 (ddd, 1 H), 8.94 (d, 1 H), 9.29 (s, 1 H).

Workup

customThe title compound was prepared
customPurification on Biotage KP-Sil
washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record: ord-d783821b628b41c79268e704099f7eef
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121271

Reaction notes

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