1-Fluoro-2-(2-nitroethenyl)benzene → HCID 15983335, compound

HRID 2220487Notes

Reaction equation

CO[CH:3](OC)[C:4]1[CH:5]=[C:6](C=[CH:18][C:19]=1[CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31])[CH2:21][N+:22]([O-])=O)[O:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.BrC1C(C(OC)OC)=CC(OCCCN2CCCCC2)=[N:39]C=1.[Li]CCCC.FC1C=CC=CC=1C=C[N+]([O-])=O>C1COCC1.C(O)(=O)C>[F:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:20]1[C:19]2[C:4](=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:39][CH:18]=2)[CH2:3][NH:22][CH2:21]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3-{3-Dimethoxymethyl-4-[1-(2-fluoro-phenyl)-2-nitro-ethyl]-phenoxy}-propyl)-piperidine. A −78° C. solution of 5-bromo-4-dimethoxymethyl-2-(3-piperidin-1-yl-propoxy)-pyridine (359 mg, 0.962 mmol) in THF (8 mL) was treated with n-BuLi (2.5 M in hexanes; 0.4 mL). After 20 min at −78° C., the mixture was treated with a solution of 1-fluoro-2-(2-nitro-vinyl)-benzene (171 mg, 1.02 mmol) in THF (5 mL). After 20 min at −78° C., the mixture was treated with acetic acid (1 mL) and was allowed to warm to 0° C. The mixture was concentrated and the residue was chromatographed (SiO2; 1-10% 2 M NH3 in MeOH/DCM) to give the title compound (285 mg, 64%) as an oil. MS (ESI): mass calcd. for C24H32FN3O5, 461.23; m/z found, 462.5 [M+H]+. 1H NMR (CDCl3): 8.03 (s, 1H), 7.30-7.24 (m, 2H), 7.15-7.03 (m, 2H), 6.95 (s, 1H), 5.55 (t, 8.2, 1H), 5.43 (s, 1H), 5.02-4.92 (m, 2H), 4.34-4.27 (m 2H), 3.35 (s, 3H), 3.27 (s, 3H), 2.55-2.42 (m, 6H), 2.05-1.95 (m, 2H), 1.69-1.60 (m, 4H), 1.49-1.42 (m, 2H).

Workup

waitAfter 20 min at −78° C.
concentrationThe mixture was concentrated
customthe residue was chromatographed (SiO2; 1-10% 2 M NH3 in MeOH/DCM)

Sources & evidence

ORD record: ord-48a37aaad1da4fdd951c6d5c5d71594c
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417054B2

Reaction notes

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