1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 56599324, compound

HRID 514057Notes

Reaction equation

HRID 514057 reaction equation
[Br:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]=[C:7]([OH:13])[CH:6]=[CH:5]2.[CH3:21][CH:22]([Si:24](Cl)([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH3:23].C1CCN2C(=NCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]=[C:7]([O:13][Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:23])[CH3:21])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139400Triisopropylsilyl chlorideHCID 67126081HCID 67126081, compound

Product 1

HCID 56599324HCID 56599324, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

6-Bromo-5-(4-chlorophenyl)-7-methylnaphthalen-2-ol (4.5 g, 12.9 mmol) was taken up in DCM (65 mL). Added to this solution were TIPSCl (4.1 mL, 19.4 mmol), DBU (3.5 mL, 23.2 mmol), and DMAP (0.16 g, 1.3 mmol). After stirring at room temperature overnight, the DCM was removed in vacuo and the residue taken up in hexane (200 mL). This solution was washed with 1 M HCl (100 mL) and the layers separated. Following extraction of the aqueous layer with hexanes, the combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The resulting residue was purified by Yamazen column chromatography (2-5% DCM/Hex) to afford 5.12 g (79%) of the title compound as a colorless syrup. 1H-NMR: 400 MHz, (CDCl3) δ: 7.61 (s, 1H); 7.49 (br d, J=8.4 Hz, 2H); 7.23 (br d, J=8.4 Hz, 2H); 7.17 (d, J=8.8 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H); 6.95 (dd, J=8.8, 2.4 Hz; 1H); 2.60 (s, 3H); 1.30 (hep, J=7.2 Hz, 3H); 1.12 (d, J=7.2 Hz, 18H).

Workup

  1. additionAdded to this solution
  2. customthe DCM was removed in vacuo
  3. washThis solution was washed with 1 M HCl (100 mL)
  4. customthe layers separated
  5. extractionextraction of the aqueous layer with hexanes
  6. washthe combined organics were washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by Yamazen column chromatography (2-5% DCM/Hex)

Sources & evidence

ORD record
ord-c1c5e8a64d8f450fba3612a947bf60c6
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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