Nicotinic Acid → HCID 54302538, compound

HRID 1954308Notes

Reaction equation

HRID 1954308 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].[C:42](O)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[N:45][CH:44]=1.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>C(Cl)Cl>[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:42]([C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1)=[O:49])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 54320327HCID 54320327, compound

Product 1

HCID 54302538HCID 54302538, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A stirred solution containing 4-[4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid tert-butyl ester (0.508 g, 0.863 mmol), nicotinic acid (0.108 g, 0.863 mmol), 2-chloro-1-methylpyridinium iodide (0.272 g, 1.04 mmol) and triethylamine (0.288 mL, 2.07 mmol) in CH2Cl2 (8.63 mL) was heated at 75° C. in a sealed tube for 3 days. The reaction was cooled to ambient temperature and concentrated. The crude product was purified on Biotage KP-Sil eluting with a 10 & 15% acetone/hexane step gradient to give 0.446 g (74%) of the title compound. 1H NMR (DMSO-d6) δ 1.35 (s, 9 H), 1.58 (s, 3 H), 2.18 (s, 6 H), 2.35 (s, 3 H), 7.18 (s, 2 H), 7.36-7.46 (m, 3 H), 7.68-7.72 (m, 1 H), 7.98 (d, 1 H), 8.15 (dd, 1 H), 8.22-8.26 (m, 2 H), 8.50-8.53 (m, 2 H), 8.95 (dd, 1 H), 9.30 (d, 1 H).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated
  3. customThe crude product was purified on Biotage
  4. washKP-Sil eluting with a 10 & 15% acetone/hexane step gradient

Sources & evidence

ORD record
ord-acaeca1e01624819a8bcc1fb4ddbc201
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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