Triethylamine → HCID 22031857, compound

HRID 634129Notes

Reaction equation

HRID 634129 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Sn:8]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH3:12])[N:3]=1.CCN(CC)CC.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>O>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Sn:8]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH3:12])[N:3]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 247870292-Bromo-6-(tributylstannyl)pyridine

Product 1

HCID 22031857HCID 22031857, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-6-(tributylstannyl)pyridine (2.0 g, 4.47 mmol) in Et3N (3.12 mL, 22.37 mmol) and was added 1-methyl piperazine (2 ml, 17.89 mmol). The reaction was heated at 100° C. for 24 h then cooled to RT, diluted with water, and extracted with EtOAc. The combined organic layer were washed with brine, dried and concentrated. The residue was purified with silica gel chromatography to give 1-methyl-4-(6-(tributylstannyl)pyridin-2-yl)piperazine (1.4 g, 70.3%). MS (ESI, pos. ion) m/z: 466.2 (M+1); 1H-NMR (CDCl3, 300 MHz) δ 7.3 (1H, t), 6.8 (1H, d), 6.5 (1H, d), 3.6 (4H, t), 2.5 (4H, t), 2.4 (3H, s), 1.5-1.7 (6H, m), 1.2-1.5 (6H, m), 1.0-1.2 (6H, q), 0.8-0.9 (9H, q).

Workup

  1. temperaturethen cooled to RT
  2. extractionextracted with EtOAc
  3. washThe combined organic layer were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-d32eb0f099f14c67a71f93b32fbc6816
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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