Pyridine → HCID 53925549, compound

HRID 1954297Notes

Reaction equation

HRID 1954297 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](Cl)(=[O:58])[C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1>C(Cl)Cl>[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:49](=[O:58])[C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 9896063HCID 9896063, compound

Product 1

HCID 53925549HCID 53925549, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At ambient temperature, to a stirred solution containing 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 (0.402 g, 0.602 mmol) and pyridine (0.292 mL, 3.61 mmol) in CH2Cl2 (6.02 mL) was added a solution of p-anisoyl chloride (0.208 g, 1.20 mmol) in CH2Cl2 (1.20 mL). After 18 h, the reaction was quenched with H2O (30 mL) and extracted with ether. The combined ethereal extracts were washed with sat. aq. NaHCO3 (3×), with sat. aq. CuSO4 (3×), with brine (3×), dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 15% acetone/hexane to give 0.354 g (73%) of the title compound. 1H NMR (DMSO-d6) δ 1.33 (s, 9 H), 1.54 (s, 3 H), 2.16 (s, 6 H), 2.34 (s, 3 H), 3.90 (s, 3 H), 7.13-7.19 (m, 4 H), 7.46-7.48 (m, 2 H), 7.60-7.70 (m, 1 H), 8.08-8.13 (m, 4 H), 8.20 (d, 2 H).

Workup

  1. customthe reaction was quenched with H2O (30 mL)
  2. extractionextracted with ether
  3. washThe combined ethereal extracts were washed with sat. aq. NaHCO3 (3×), with sat. aq. CuSO4 (3×), with brine (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified on Biotage KP-Sil
  7. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-48d54825707c4d16b59465db869dc098
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

Loading…