2-(Tributylstannyl)pyridine → HCID 68312888, compound

HRID 1530381Notes

Reaction equation

HRID 1530381 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[N:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)[CH:9]=[C:8](I)[N:7]=3.C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)CCC>CN(C=O)C.[Cu](I)I>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[N:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)[CH:9]=[C:8]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[N:7]=3

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 582048589-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

Product 1

HCID 68312888HCID 68312888, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-bromo-2-iodo-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (300 mg, 0.767 mmol), 2-tributylstannanylpyridine (339 mg, 0.921 mmol), Pd2(PPh3)2Cl2 (54 mg, 0.077 mmol) and copper iodide (44 mg, 0.23 mmol) in DMF (6 mL) was purged with nitrogen and then heated at 100° C. for 1 h using microwave irradiation. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were concentrated in vacuo and the resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM followed by Si-PCC, gradient 0-2% 2M NH3/MeOH in DCM) affording the title compound as a white solid (192 mg, 73%). LCMS: RT 3.37 min [M+H]+ 341.9/343.9

Workup

  1. customwas purged with nitrogen
  2. custommicrowave irradiation
  3. washwas washed with MeOH
  4. washthe product eluted with 2M NH3/MeOH
  5. additionThe product containing fractions
  6. concentrationwere concentrated in vacuo
  7. customthe resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM followed by Si-PCC, gradient 0-2% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-312cf178b91b451492b2c97a7e90daaa
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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