Ethyl 3-amino-4-fluorobenzoate → HCID 11189594, compound

HRID 733634Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[NH2:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][C:32]=1[F:33])[C:25]([O:27][CH2:28][CH3:29])=[O:26]>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:21][C:22]3[CH:23]=[C:24]([CH:30]=[CH:31][C:32]=3[F:33])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 18412404Ethyl 3-amino-4-fluorobenzoate

HCID 73697410HCID 73697410, compound

Product 1

HCID 11189594HCID 11189594, compound

Procedure

The titled compound was prepared following the procedure A using 4-[(4-butylphenyl)ethenyl]benzaldehyde and ethyl 3-amino-4-fluorobenzoate as a pale yellow oil (61%). 1H NMR (CDCl3, 300 MHz) δ 7.49 (d, J=8.3 Hz, 2H), 7.42 (d, J=7.9 Hz, 2H), 7.35 (m, 4H), 7.14 (d, J=7.9 Hz, 2H), 7.00 (dd, J=11.0, 8.7 Hz, 1H), 4.41 (brs, 2H), 4.30 (q, J=7.2 Hz, 2H), 2.60 (t, J=7.7 Hz, 2H), 1.69-1.53 (m, 4H), 1.34 (t, J=7.2 Hz, 3H), 0.91 (t, J=7.4 Hz, 3H). HPLC, Rt: 5.87 min (Purity: 94.3%).

Sources & evidence

ORD record: ord-6a8bb39739424a7690e77d2e4f554438
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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