Cesium carbonate → HCID 86723383, compound

HRID 508542Notes

Reaction equation

HRID 508542 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:11])(F)F)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:41][C:42]([CH3:46])([CH3:45])[CH2:43][NH2:44]>CS(C)=O>[C:42]([C:43]1[C:8]([F:11])=[C:7]([NH:12][C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[C:5]([CH:4]([O:3][CH2:1][CH3:2])[O:32][CH2:33][CH3:34])[N:44]=1)([CH3:46])([CH3:45])[CH3:41]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79882NeopentylamineHCID 86723378HCID 86723378, compound

Product 1

HCID 86723383HCID 86723383, compoundYield 101.8%

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 (2.328 g, 5 mmol), cesium carbonate (4.07 g, 12.50 mmol), 2,2-dimethylpropan-1-amine (1.307 g, 15.00 mmol) and anhydrous DMSO (20 mL) gave 2-(tert-butyl)-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine (2.61 g, 97%) as an off-white solid: mp 168-169.5° C.; 1H NMR (400 MHz, CDCl3) δ 7.28 (m, 15H), 6.16 (d, J=6.1 Hz, 1H), 5.71 (d, J=5.2 Hz, 1H), 5.01 (s, 1H), 3.29 (dd, J=9.5, 7.1 Hz, 2H), 3.17 (dq, J=9.4, 7.0 Hz, 2H), 1.36 (d, J=1.3 Hz, 9H), 1.01 (t, J=7.0 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 151.67 (d, J=9.9 Hz), 150.42 (d, J=5.9 Hz), 147.83 (d, J=249.5 Hz), 144.45, 141.00 (d, J=10.3 Hz), 128.91, 128.14, 127.12, 107.63, 102.63, 71.04, 61.35, 36.75 (d, J=5.1 Hz), 29.00 (d, J=3.5 Hz), 15.09; 19F NMR (376 MHz, CDCl3) δ −145.99; HRMS-ESI (m/z) [M+H]+ calcd for C33H37FN2O3, 512.2839. found, 512.2851.

Sources & evidence

ORD record
ord-9b04246493ff44b2a28af6cc4af190fd
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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