Potassium Carbonate → HCID 58366252, compound

HRID 877392Notes

Reaction equation

HRID 877392 reaction equation
[Si:1]([O:8][CH:9]([C:22]1[N:23]=[N:24][NH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C([O-])([O-])=O.[K+].[K+].CN(C)CCN>CN(C=O)C.CCOC(C)=O.[Cu]I>[Si:1]([O:8][CH:9]([C:22]1[N:23]=[N:24][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 2211262-IodopyridineHCID 58366231HCID 58366231, compound

Product 1

HCID 58366252HCID 58366252, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In a gas tight vessel, a solution of 5-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-2H-tetrazole (16 mg, 0.043 mmol), 2-iodopyridine (7 μL, 0.064 mmol), CuI (1 mg, 0.004 mmol), K2CO3 (12 mg, 0.085 mmol), and N,N-dimethylethylene diamine (1 μL, 0.006 mmol) in DMF (200 μL) was purged with Ar and sealed. The reaction mixture was warmed at 100° C. for 18 h before it was cooled to room temperature, diluted with EtOAc, and washed with H2O, 9:1 NH4OH: saturated aqueous NH4Cl, and saturated aqueous NaCl. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure to afford the crude material that was purified by flash chromatography (SiO2, 1.5×15 cm, 5-10% acetone-hexanes) to afford 2-(5-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-2H-tetrazol-2-yl)-pyridine (4.0 mg, 21%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 8.69 (dd, 1H, J=0.9, 4.8 Hz), 8.16 (d, 1H, J=7.5 Hz), 7.98 (dt, 1H, J=1.8, 7.9 Hz), 7.48 (m, 1H), 7.26 (m, 2H), 7.16 (m, 3H), 5.16 (dd, 1H, J=5.9, 7.4 Hz), 2.58 (t, 2H, J=7.7 Hz), 1.99 (m, 2H), 1.60 (m, 2H), 1.34 (m, 6H), 0.88 (s, 9H), 0.10 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 169.7, 149.6, 149.0, 142.9, 139.5, 128.5, 128.4, 125.7, 125.0, 115.2, 67.4, 37.5, 36.1, 31.5, 29.3, 25.9 (3C), 25.4, 18.4, −4.1, −4.8; HRMS-ESI-TOF m/z 452.2823 ([M+H]+, C25H37N5OSi requires 452.2840).

Workup

  1. customsealed
  2. temperaturewas cooled to room temperature
  3. washwashed with H2O, 9:1 NH4OH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customto afford the crude material that
  7. customwas purified by flash chromatography (SiO2, 1.5×15 cm, 5-10% acetone-hexanes)

Sources & evidence

ORD record
ord-b0e879f6dcfb489ba8f335ff2471740b
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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