2-(Tributylstannyl)pyridine → (4-Methyl-pyridin-2-yl)-[6-(2-pyridin-2-yl-oxazol-5-yl)-pyridin-2-yl]-amine

HRID 1854611Notes

Reaction equation

HRID 1854611 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.C([Sn](CCCC)(CCCC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:4]3[O:3][C:2]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[N:6][CH:5]=3)[N:12]=2)[CH:19]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 53311311HCID 53311311, compound

Product 1

HCID 53312249(4-Methyl-pyridin-2-yl)-[6-(2-pyridin-2-yl-oxazol-5-yl)-pyridin-2-yl]-amineYield 31.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (44 mg, 0.153 mmol), 2-tri-n-butylstannyl pyridine (68 mg, 0.184 mmol) and Pd(PPh3)4 (18 mg, 0.016 mmol) in toluene (4 ml) was heated to reflux for 18 h and then concentrated in vacuo. The residue was purified by column chromatography on SiO2 eluting with 5% EtOH in DCM to afford the title compound as a pale orange solid (16 mg, 31%). 1H NMR (300 MHz, DMSO-d6): δ=9.85 (s, 1H), 8.76 (d, J=5.0 Hz, 1H), 8.21 (d, J=7.8 Hz, 1H), 8.12 (d, J=5.0 Hz, 1H), 8.03 (t, J=7.8 Hz, 1H), 7.94 (s, 1H), 7.91 (s, 1H), 7.80 (t, J=7.8 Hz, 1H), 7.67 (d, J=8.5, 1H), 7.58 (m, 1H), 7.39 (d, J=7.2 Hz, 1H), 6.78 (d, J=5.0 Hz, 1H), 2.38 (s, 3H). (ESI+) m/z 330 (M+H)+. Retention time=2.29 mins (method 1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on SiO2 eluting with 5% EtOH in DCM

Sources & evidence

ORD record
ord-d1878a06fc954213bacb729bf9a4482d
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

Loading…