Potassium Carbonate → HCID 10168863, compound

HRID 1582845Notes

Reaction equation

HRID 1582845 reaction equation
[C:1]1([CH2:17][NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.Br[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[B:34]1[O:39]CCC[O:35]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:17]([N:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[B:34]([OH:35])[OH:39])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N:18]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[B:34]([OH:39])[OH:35])[CH2:17][C:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1)[C:1]1[CH:14]=[CH:15][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4198002HCID 4198002, compoundHCID 14762973HCID 14762973, compound

Product 1

HCID 10168863HCID 10168863, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-pyren-1-ylmethyl-hexane-1,6-diamine (291 mg, 0.69 mmol), 2-(2-bromomethyl-phenyl)-[1,3,2]dioxaborinane (422 mg, 1.66 mmol), and potassium carbonate (380 mg, 2.76 mmol) in dry acetonitril (10 ml) was heated at reflux for 20 hours under nitrogen atmosphere. The solvent was removed under vacuum, the residue was dissolved in chloroform and washed with water. The solvent was dried over magnesium sulphate and removed under vacuum. The residue was dissolved in THF (10 ml). Water (10 ml) was added to the THF solution, and the solution was stirred at room temperature for 3 hours. Organic phase was extracted with chloroform, washed with water, and dried over magnesium sulphate. The solvent was removed under vacuum. The residue was reprecipitated from chloroform with n-hexane to give a white yellow powder (172 mg, 35%). 1H NMR (CDCl3) δ/ppm 1.25-1.48 (8H, m, (CH2)4), 2.25 (2H, t, BnNCH2), 2.48 (2H, t, PyCNCH2), 3.45 (2H, s, PhB(OH)CH2NBn), 3.58 (2H, s, PhB(OH)CH2NCPy), 3.85 (2H, s, PhCH2), 4.21 (2H, s, PyCH2), 7.02-7.41 and 7.88-8.19 (22H m, Ar-H), 8.86 (4H, bs, BOH). 13C NMR (CDCl3) δ/ppm 51.69, 52.99, 54.42, 56.42, 57.11, 61.03, 61.86, 67.85, 122.90, 124.55, 124.99, 125.79, 127.31, 128.28, 128.57, 129.43, 130.00, 130.55, 136.32, 141.56; Found: C, 76.56; H, 6.69; N, 3.80, C44H46B2N2O4 requires C, 76.76; H, 6.73 N, 4.07%; m/z (FAB) 1230 ([M+H+4(3-HOCH2C6H4NO2)-4(H2O)]+, 100%); mp. 165-168° C.

Workup

  1. temperatureat reflux for 20 hours under nitrogen atmosphere
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with water
  5. dry with materialThe solvent was dried over magnesium sulphate
  6. customremoved under vacuum
  7. dissolutionThe residue was dissolved in THF (10 ml)
  8. additionWater (10 ml) was added to the THF solution
  9. extractionOrganic phase was extracted with chloroform
  10. washwashed with water
  11. dry with materialdried over magnesium sulphate
  12. customThe solvent was removed under vacuum
  13. customThe residue was reprecipitated from chloroform with n-hexane

Sources & evidence

ORD record
ord-291753798edc4e6f8ecf0ef314ff5198
Source dataset
uspto-grants-2004_05
Patent number
US06740257B2

Reaction notes

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