Pyridine → HCID 53714433, compound

HRID 1954310Notes

Reaction equation

HRID 1954310 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].N1C=CC=CC=1.[C:49]1([CH2:55][C:56](Cl)=[O:57])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>>[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:56](=[O:57])[CH2:55][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 9896063HCID 9896063, compound

Product 1

HCID 53714433HCID 53714433, compoundYield 51%

Procedure

The title compound was prepared according to the procedure in Example 17, 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), pyridine (0.335 mL, 4.15 mmol) and phenylacetylchloride (0.183 mL, 1.38 mmol). Purification on Biotage KP-Sil eluting with 3% EtOAc/pet. ether gave 0.272 g (51%) of the title compound. 1H NMR (DMSO-d6) δ 1.51 (s, 9 H), 1.56 (s, 3 H), 2.14 (s, 6 H), 2.43 (s, 3 H), 4.04 (s, 2 H), 7.18 (s, 2H), 7.27-7.37 (m, 5 H), 7.46-7.49 (m, 2 H), 7.66 (ddd, 1 H), 8.01-8.07 (m, 2 H), 8.13-8.21 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-0a25e96a917140ac9d522680f866d540
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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