2-Chloro-4-fluoropyridine → HCID 16110622, compound

HRID 605658Notes

Reaction equation

HRID 605658 reaction equation
[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([Sn](CCCC)(CCCC)CCCC)=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][N:42]=1>>[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([C:41]2[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][N:42]=2)=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 27827922-Chloro-4-fluoropyridineHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110622HCID 16110622, compoundYield 51%

Procedure

The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (130 mg, 0.196 mmol) and 2-chloro-4-fluoropyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (48 mg, 51%): 1H NMR (CDCl3, 400 MHz) δ 8.59 (dd, 1H, J=8.5, 5.6 Hz), 7.69 (s, 1H), 7.38 (dd, 1H, J=9.4, 2.3 Hz), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 6.96 (ddd, 1H, J=8.2, 5.6, 2.4 Hz), 4.87 (dd, 1H, J=7.0, 6.2 Hz), 2.60 (t, 2H, J=7.6 Hz), 1.96 (m, 2H), 1.62 (m, 2H), 1.36 (m, 4H), 0.91 (s, 9H), 0.11 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 170.4, 167.8, 166.1, 152.4 (d, J=7.6 Hz), 150.2, (d, J=7.6 Hz), 149.8 (d, J=4.6 Hz), 142.7, 128.3, 128.2, 126.2, 125.5, 110.5 (d, J=15.2 Hz), 106.9 (d, J=18.2 Hz), 68.7, 36.4, 35.9, 31.4, 29.1, 25.7, 25.7, 25.1, 18.2, −5.0, −5.2.

Sources & evidence

ORD record
ord-80b369e8596c46ed8627b50e5c665d63
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

Loading…