4-(Trifluoromethyl)aniline → HCID 67186828, compound

HRID 735910Notes

Reaction equation

[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[F:19][C:20]([F:29])([F:28])[C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>>[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:25][C:24]2[CH:26]=[CH:27][C:21]([C:20]([F:19])([F:28])[F:29])=[CH:22][CH:23]=2)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 2

HCID 99644-(Trifluoromethyl)aniline

HCID 578413204-Dec-1-ynylbenzaldehyde

Product 1

HCID 67186828HCID 67186828, compoundYield 50%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 4-dec-1-ynylbenzaldehyde and 4-(trifluoromethyl)aniline gave the title compound as a colorless oil (50%). 1H NMR (CDCl3, 300 MHz) δ 7.32 (d, J=8.3 Hz, 2H), 7.29 (d, J=8.3 Hz, 2H), 7.21-7.13 (m, 2H), 6.50 (d, J=8.7 Hz, 2H), 4.28 (s, 2H), 2.32 (t, J=7.2 Hz, 2H), 1.60-1.43 (m, 2H), 1.43-1.31 (m, 2H), 1.30-1.11 (m, 8H), 0.87-0.75 (m, 3H). M−(LC/MS(ESI)): 386.4. HPLC (Condition A), Rt: 6.43 min (HPLC purity: 82.6%).

Workup

customThe same procedure as employed in the preparation of Example 226 (step a) but

Sources & evidence

ORD record: ord-3155d085f7b44b819214a54672b9bb87
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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