Methyl 2-chloronicotinate → HCID 16110712, compound

HRID 605644Notes

Reaction equation

HRID 605644 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[N:36]=[CH:35][CH:34]=[CH:33][C:28]=2[C:29]([O:31][CH3:32])=[O:30])=[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.ClC1N=CC=CC=1C(OC)=O>>[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[N:36]=[CH:35][CH:34]=[CH:33][C:28]=3[C:29]([O:31][CH3:32])=[O:30])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 819931Methyl 2-chloronicotinateHCID 16110686HCID 16110686, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110712HCID 16110712, compoundYield 94%

Procedure

Methyl 2-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)nicotinate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (83 mg, 0.125 mmol) and methyl 2-chloronicotinate following General Procedure A. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a white solid (60 mg, 94%): 1H NMR (CDCl3, 500 MHz) δ 8.80 (dd, 1H, J=6.4, 3.0 Hz), 8.02 (dd, 1H, J=10.0, 6.0 Hz), 7.72 (s, 1H), 7.39-7.32 (m, 3H), 7.25-7.23 (m, 3H), 4.91 (t, 1H, J=7.0 Hz), 4.01 (s, 3H), 2.66 (t, 2H, J=7.5 Hz), 2.03-1.91 (m, 2H), 1.74-1.68 (m, 2H), 1.46-1.35 (m, 6H), 0.96 (s, 9H), 0.17 (s, 3H), 0.05 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 168.0, 166.5, 151.5, 149.9, 145.2, 143.2, 137.5, 128.8, 128.6, 128.0, 126.4, 126.0, 122.7, 69.1, 53.3, 37.0, 36.3, 31.8, 29.6, 26.2, 26.2, 25.5, 18.6, −4.5, −4.8.

Sources & evidence

ORD record
ord-524e95eac27f4ccd8e629f34e2c63be8
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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