Water → HCID 23025715, compound

HRID 1437484Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=3)[O:8][C:4]=2[CH:3]=1.I[CH:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:19]([CH3:21])[CH3:20])[CH:10]=3)[O:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(6-bromobenzoxazol-2-yl)phenol (Compound of Example 272) (1.02 g) in N,N-dimethyl formamide (6 ml) were added 2-iodopropane (0.68 g) and potassium carbonate (0.63 g) at 50° C., and the mixture was stirred at 50° C. for 1.5 hour. To the mixture were further added 2-iodopropane (0.34 g) and potassium carbonate (0.31 g), and the mixture was further stirred at 50° C. for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography. The fraction eluted with ethyl acetate-hexane (1:20 to 1:6, v/v) was concentrated under reduced pressure to isolate 6-bromo-2-(3-isopropoxyphenyl)benzoxazole (896 mg, 77%).

Workup

stirringthe mixture was further stirred at 50° C. for 1 hour
extractionextracted with ethyl acetate-tetrahydrofuran (3:1
washThe organic layer was washed with water
dry with materialdried over MgSO4
distillationThe solvent was distilled off under reduced pressure
washThe fraction eluted with ethyl acetate-hexane (1:20 to 1:6, v/v)
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-a9f6411212394dc381d3a5ed5d87ba16
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622479B2

Reaction notes

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