2-Chlorobenzoxazole → N-(4-(3-Bromopyridin-2-yloxy)phenyl)benzo[D]oxazol-2-amine

HRID 410219Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CN1C(=O)CCC1>[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:17]3[O:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 4-(3-bromopyridin-2-yloxy)aniline (1.73 g, 6.53 mmol) and 2-chlorobenzoxazole (1.00 g, 6.51 mmol, TCI America) in NMP (3 mL) was sealed in a screw-cap flask and heated at 170° C. for 20 h. The reaction was cooled to rt and partitioned with water/EtOAc. The aqueous layer was extracted with EtOAc (3×) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco (80 gram)) eluting with EtOAc:hexanes (0:1→1:2) a tan amorphous solid. MS (ESI, pos. ion) m/z: 382.0, 383.9 (M+1).

Workup

customwas sealed in a screw-cap flask
temperatureThe reaction was cooled to rt
custompartitioned with water/EtOAc
extractionThe aqueous layer was extracted with EtOAc (3×)
customthe combined organic layers were evaporated onto silica gel
custompurified by flash chromatography (Isco (80 gram))
washeluting with EtOAc:hexanes (0:1→1:2) a tan amorphous solid

Sources & evidence

ORD record: ord-0a1c26e21c5b4b2c8cab14aeba7d1d3d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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