1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 1-(5-Nitro-1-benzofuran-7-yl)-3-(trifluoromethyl)piperazine

HRID 1162018Notes

Reaction equation

I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+].[F:62][C:63]([F:71])([F:70])[CH:64]1[CH2:69][NH:68][CH2:67][CH2:66][NH:65]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].C1(C)C(C)=CC=CC=1>[N+:11]([C:4]1[CH:3]=[C:2]([N:68]2[CH2:67][CH2:66][NH:65][CH:64]([C:63]([F:71])([F:70])[F:62])[CH2:69]2)[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-:13])=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To 7-iodo-5-nitro-1-benzofuran (231.4 mg, 0.08 mmol) the following was added: Xantphos (92.6 mg, 0.16 mmol), Pd2 dba3 (36.6 mg, 0.04 mmol), sodium tert-butoxide (215.4 mg, 2.24 mmol), 2-(trifluoromethyl)piperazine (148.1 mg, 0.96 mmol; Intermediate 45) and xylene (23 mL). The resulting mixture was stirred at 100° C. for 3 days. Filtration through Celite and purification by flash chromatography, using EtOAc:heptane (1:1) as eluent, furnished 1-(5-nitro-1-benzofuran-7-yl)-3-(trifluoromethyl)piperazine (112 mg, 44% yield). HPLC 90%, RT=1.648 min (System A; 10-97% MeCN over 3 min), MS (ESI+) m/z 316 (M+H)+.

Workup

filtrationFiltration
customthrough Celite and purification by flash chromatography

Sources & evidence

ORD record: ord-5c9f574fd9e94c288783540fd302b1d1
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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