Hexanal → Methyl 5-{[4-[(4-butylphenyl)ethynyl](hexyl)anilino]methyl}-2-fluorobenzoate

HRID 551974Notes

Reaction equation

HRID 551974 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][C:5]=1[F:12].[CH2:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17].[CH:33](=O)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>>[CH2:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:27]=[CH:28][C:29]([N:32]([CH2:10][C:8]3[CH:7]=[CH:6][C:5]([F:12])=[C:4]([CH:9]=3)[C:3]([O:2][CH3:1])=[O:13])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:30][CH:31]=2)=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 6184HexanalHCID 24971957Methyl 2-fluoro-5-formylbenzoateHCID 575545094-(4-Butylphenylethynyl)phenylamine

Product 1

HCID 57554526Methyl 5-{[4-[(4-butylphenyl)ethynyl](hexyl)anilino]methyl}-2-fluorobenzoateYield 85%

Procedure

The title compound was prepared following procedure described in Example 49, step a) from 2-fluoro-5-formylbenzoic acid methyl ester (302 mg; 1.66 mmol), 4-(4-butylphenylethynyl)phenylamine (413 mg; 1.66 mmol) and hexanal (Aldrich, 600 μl; 4.97 mmol). Purification of the crude (890 mg) by flash chromatography using silicagel (EtOAc/c-Hex 5:95 then 10:90) afforded 700 mg (85%) of the title compound as a white powder. HPLC, Rt: 6.62 min (purity: 100%), LC/MS, M+(ESI): 500.3, 1H NMR(CDCl3) δ: 7.75 (dd, J=6.8, 2.3 Hz, 1H), 7.37 (d, J=8.3 Hz, 2H), 7.32 (d, J=8.9 Hz, 2H), 7.20 (m, 1H), 7.10 (d, J=8.3 Hz, 2H), 7.05 (dd, J=10.5, 8.6 Hz, 1H), 6.58 (d, J=7.9 Hz, 2H), 4.52 (s, 2H), 3.90 (s, 3H), 3.38 (t, J=7.8 Hz, 2H), 2.57 (t, J=7.6 Hz, 2H), 1.57 (m, 4H), 1.30 (m, 8H), 0.87 (m, 6H).

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification of the crude (890 mg) by flash chromatography

Sources & evidence

ORD record
ord-d40a30ad6db442c8aaa654c12975aa63
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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