p-Fluorophenethylamine → HCID 86723384, compound

HRID 508543Notes

Reaction equation

HRID 508543 reaction equation
[CH2:1]([O:3][CH:4]([O:32][CH2:33][CH3:34])[C:5]#[C:6][C:7](=[N:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8](F)(F)[F:9])[CH3:2].[F:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][NH2:44])=[CH:38][CH:37]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH2:33]([O:32][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[N:44]=[C:43]([CH2:42][C:39]2[CH:40]=[CH:41][C:36]([F:35])=[CH:37][CH:38]=2)[C:8]([F:9])=[C:7]([NH:12][C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1)[CH3:34]

Participants

5

Reactant 3

HCID 4653p-FluorophenethylamineHCID 10796Cesium carbonateHCID 86723378HCID 86723378, compound

Product 1

HCID 86723384HCID 86723384, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using the procedure of Example 9, N-(5,5-diethoxy-1,1,1-trifluoropent-3-yn-2-ylidene)-1,1,1-triphenylmethanamine (4.66 g, 10 mmol), 2-(4-fluorophenyl)ethanamine (1.670 g, 12.00 mmol), cesium carbonate (8.15 g, 25.00 mmol) and DMSO (30 mL) gave 6-(diethoxymethyl)-3-fluoro-2-(4-fluorobenzyl)-N-tritylpyridin-4-amine (3.25 g, 56.4%) as a yellow glass, which crystallized from CH3CN (25 mL): mp 129-130° C.; 1H NMR (400 MHz, CDCl3) δ 7.27 (m, 19H), 6.94 (m, 2H), 6.19 (d, J=6.6 Hz, 1H), 5.71 (d, J=4.3 Hz, 1H), 5.06 (s, 1H), 4.05 (d, J=2.9 Hz, 2H), 3.23 (dq, J=9.4, 7.1 Hz, 2H), 3.13 (dq, J=9.4, 7.0 Hz, 2H), 1.00 (t, J=7.0 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 161.48 (d, J=243.8 Hz), 152.10 (d, J=5.9 Hz), 147.04 (d, J=246.0 Hz), 144.65 (d, J=13.9 Hz), 144.13, 140.88 (d, J=9.4 Hz), 134.69 (d, J=3.1 Hz), 130.28 (d, J=7.8 Hz), 128.86, 128.20, 127.24, 114.99 (d, J=21.2 Hz), 108.23, 101.87, 71.24, 61.05, 37.45, 15.05; 19F NMR (376 MHz, CDCl3) δ−117.27, −151.26 (dd, J=6.6, 3.6 Hz); HRMS-ESI (m/z) [M+H]+ calcd for C36H34F2N2O2, 564.2588. found, 564.2595.

Sources & evidence

ORD record
ord-880f3ccd8e68496d80fc46abf74a492e
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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