4-[2-(4-Butylphenyl)ethynyl]benzaldehyde → Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate

HRID 733629Notes

Reaction equation

HRID 733629 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C: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]=[CH:24][C:25]([F:32])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28]>>[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]=[CH:24][C:25]([F:32])=[C:26]([CH:31]=3)[C:27]([O:29][CH3:30])=[O:28])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 113345124-[2-(4-Butylphenyl)ethynyl]benzaldehydeHCID 15621043Methyl 5-amino-2-fluorobenzoate

Product 1

HCID 11452740Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate

Procedure

The titled compound was prepared following the procedure A using 4-[(4-butylphenyl)ethynyl]benzaldehyde and methyl 5-amino-2-fluorobenzoate as a white powder (74%). 1HNMR (CDCl3, 300 MHz) δ 7.51 (d, J=7.9 Hz, 2H), 7.45 (d, J=8.0 Hz, 2H), 7.34 (d, J=8.0 Hz, 2H), 7.17 (m, 3H), 6.97 (m, 1H), 6.76 (m, 1H), 4.35 (s, 2H), 3.92 (s, 3H), 2.63 (t, J=7.8 Hz, 2H), 1.61 (m, 2H), 1.37 (m, 2H), 0.94 (t, J=7.4 Hz, 3H). M+ (ESI): 414.0. HPLC, Rt: 5.78 min (Purity: 98.2%).

Sources & evidence

ORD record
ord-d114f2a4aee54f97b2049e1e632243e6
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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