Toluene → (4-Methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine

HRID 1854592Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[N:3]=1.[NH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1.CC([O-])(C)C.[Na+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[O:12][CH:11]=[N:10][CH:9]=3)[N:3]=2)[CH:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A sealed tube with a teflon screw cap was charged with 2-bromo-6-oxazol-5-ylpyridine (4.00 g, 17.8 mmol), 2-amino-4-methylpyridine (2.30 g, 21.3 mmol), Pd2(dba)3 (320 mg, 0.349 mmol), (±)-BINAP (440 mg, 0.707 mmol), NaOtBu (2.40 g, 25.0 mmol) and anhydrous toluene (80 ml) and heated to 90° C. with stirring for 1 h. The cooled reaction mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2, eluting with 30% EtOAc in cyclohexane to afford the title compound as a yellow-orange solid (1.89 g, 42%). 1H NMR (300 MHz, DMSO-d6): δ=9.78 (s, 1H), 8.53 (s, 1H), 8.11 (d, J=5.0 Hz, 1H), 7.84-7.59 (m, 4H), 7.25 (d, J=7.3 Hz, 1H), 6.76 (d, J=5.0 Hz, 1H), 2.32 (s, 3H). (ESI+) m/z 253 (M+H).

Workup

customThe cooled reaction mixture
extractionextracted with DCM
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
customevaporated under reduced pressure before purification by column chromatography on SiO2
washeluting with 30% EtOAc in cyclohexane

Sources & evidence

ORD record: ord-235405429eaf4217a6c9b0e302fffaad
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962665B2

Reaction notes

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