HCID 10163059, compound → HCID 10162253, compound

HRID 860571Notes

Reaction equation

HRID 860571 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29]4[S:33][C:32](=[O:34])[NH:31][C:30]4=[O:35])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17]C)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>C(Cl)Cl>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29]4[S:33][C:32](=[O:34])[NH:31][C:30]4=[O:35])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[OH:17])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

3

Reactant 1

HCID 10163059HCID 10163059, compound

Product 1

HCID 10162253HCID 10162253, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[6-(3-[1-adamantyl]-4-methoxyphenyl)-naphthalen-2-yl]-2,4-thiazolidinedione (0.130 g, 0.27 mmol) in 10 mL of anhydrous CH2Cl2 cooled to −78° C. under argon was added borontribromide (0.31 mL, 3.23 mmol). The cooling bath was removed and the reaction mixture was stirred for 18 hours at RT. The resulting mixture was carefully poured onto ice and extracted with CH2Cl2 (2×50 mL). The combined organics were washed with water, brine and dried over magnesium sulfate. The mixture was filtered, evaporated and the residue was purified on silica gel (eluent: hexane:EtOAc, 3:2) to give 5-[6-(3-[1-adamantyl]-4-hydroxyphenyl)-naphthalen-2-yl]-2,4-thiazolidinedione as a solid (0.090 g, 72% yield); mp 312–314.5° C., 1H NMR (300 MHz; DMSO-d6): δ 1.74 (s, 6H), 2.05–2.15 (m, 9H), 5.97 (s, 3H), 6.88 (d, J=8.1 Hz, 1H), 7.43–7.51 (m, 3H), 7.81 (dd, J1=8.7 Hz, J2=1.8 Hz 1H), 7.94–8.02 (m, 3H), 8.10 (s, 1H), 9.52 (s, 1H), 12.35 (brs, 1H).

Workup

  1. additionwas added borontribromide (0.31 mL, 3.23 mmol)
  2. customThe cooling bath was removed
  3. additionThe resulting mixture was carefully poured onto ice
  4. extractionextracted with CH2Cl2 (2×50 mL)
  5. washThe combined organics were washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customevaporated
  9. customthe residue was purified on silica gel (eluent: hexane:EtOAc, 3:2)

Sources & evidence

ORD record
ord-e4851c54b9f34e14b84b291c11ee124e
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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