Methyl 6-chloropyridine-3-carboxylate → HCID 16110713, compound

HRID 605641Notes

Reaction equation

HRID 605641 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][N:28]=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(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=CC(C(OC)=O)=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:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][N:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 16110687HCID 16110687, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110713HCID 16110713, compoundYield 72%

Procedure

Methyl 6-(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 6-chloronicotinate following General Procedure A. Flash chromatography (5-10% EtOAc/hexanes) yielded the title compound as a clear oil (46 mg, 72%): 1H NMR (CDCl3, 500 MHz) δ 9.28 (d, 1H, J=2.0 Hz), 8.43 (dd, 1H, J=10.0, 6.0 Hz), 7.84 (s, 1H), 7.78 (d, 1H, J=8.5 Hz), 7.35-7.32 (m, 2H), 7.25-7.22 (m, 3H), 4.95 (t, 1H, J=7.0 Hz), 4.04 (s, 3H), 2.67 (t, 2H, J=7.5 Hz), 2.05-1.98 (m, 2H), 1.74-1.67 (m, 2H), 1.48-1.40 (m, 6H), 0.98 (s, 9H), 0.18 (s, 3H), 0.08 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 167.1, 165.8, 151.6, 151.0, 150.5, 143.2, 138.5, 128.8, 128.6, 127.9, 126.0, 125.0, 118.7, 69.2, 52.9, 36.9, 36.3, 31.8, 29.6, 26.1, 26.1, 25.5, 18.6, −4.5, −4.7.

Sources & evidence

ORD record
ord-8a18c1342b5f43628095b66f314485fa
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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