Isonicotinic Acid → HCID 54201787, compound

HRID 1954311Notes

Reaction equation

HRID 1954311 reaction equation
[C:1]([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])([CH3:4])([CH3:3])[CH3:2].[C:43](O)(=[O:50])[C:44]1[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=1.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>>[C:1]([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[O:41][C:43]([C:44]1[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=1)=[O:50])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 9896063HCID 9896063, compound

Product 1

HCID 54201787HCID 54201787, compoundYield 86.3%

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, 0.691 mmol), isonicotinic acid (0.0851 g, 0.691 mmol), 2-chloro-1-methylpyridinium iodide (0.212g, 0.829 mmol) and triethylamine (0.327 mL, 2.35 mmol). Purification on Biotage KP-Sil eluting with 25% EtOAc/hexane gave 0.461 g (86%) of the title compound. 1H NMR (DMSO-d6) δ 1.35 (s, 9 H), 1.54 (s, 3 H), 2.17 (s, 6 H), 2.36 (s, 3 H), 7.19 (s, 2 H0, 7.45-7.47 (m, 2 H), 7.61-7.66 (m, 1 H), 8.04 (dd, 2 H), 8.13-8.25 (m, 4 H), 8.92 (dd, 2 H). mass spectrum (+ESI) m/z 772/774 (M+H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-699e4de6e6cb4a4dad4b567d171e28e6
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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