Toluene → HCID 67354815, compound

HRID 522931Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[F:9][C:10]1[CH:20]=[CH:19][C:13]([O:14][CH:15]2[CH2:18][NH:17][CH2:16]2)=[CH:12][CH:11]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=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]>[Br:8][C:4]1[CH:3]=[C:2]([N:17]2[CH2:18][CH:15]([O:14][C:13]3[CH:12]=[CH:11][C:10]([F:9])=[CH:20][CH:19]=3)[CH2:16]2)[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1, 3-dibromobenzene (500 mg, 2.13 mmol) and 3-(4-fluorophenoxy)azetidine (357 mg, 2.13 mmol) in toluene (7 mL, 3 mmol) was added cesium carbonate (600 mg, 5.3 mmol) and degassed for 15 min. Pd2(dba)3 (97 mg, 0.106 mmol) and BINAP (66 mg, 0.106 mmol) were added and the mixture was heated in the microwave for 30 min at 100° C. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×30 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 1-(3-bromophenyl)-3-(4-fluorophenoxy)azetidine (200 mg, 30%) as a solid. Observed mass (M+1): 322.1.

Workup

customdegassed for 15 min
concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with EtOAc (2×30 mL)
washThe organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-8885093045b5433bb7d6a5a19411150c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

Loading…