2-Chloro-4-cyanopyridine → HCID 16110652, compound

HRID 605655Notes

Reaction equation

HRID 605655 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][N:34]=2)[C:30]#[N:31])=[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(C)(C)C)(C)C.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.ClC1C=C(C#N)C=CN=1>>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][N:34]=3)[C:30]#[N:31])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 5686382-Chloro-4-cyanopyridineHCID 16110684HCID 16110684, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110652HCID 16110652, compoundYield 75%

Procedure

2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)isonicotinonitrile. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (110 mg, 0.166 mmol) and 2-chloro-4-cyanopyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (72 mg, 75%): 1H NMR (CDCl3, 400 MHz) δ 8.79 (dd, 1H, J=5.0, 0.9 Hz), 7.84 (s, 1H), 7.74 (s, 1H), 7.43 (dd, 1H, J=5.0, 1.4 Hz), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 4.88 (dd, 1H, J=7.3, 6.6 Hz), 2.60 (t, 2H, J=7.8 Hz), 1.93 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.91 (s, 9H), 0.12 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.7, 150.8, 149.0, 148.6, 142.7, 128.3, 128.2, 127.1, 125.5, 123.7, 121.4, 120.2, 116.1, 68.6, 36.4, 35.8, 31.3, 29.0, 25.6, 25.6, 25.0, 18.1, −5.0, −5.2.

Sources & evidence

ORD record
ord-51a5ebb209d64efc88a1c9d6d03d41dc
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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