Methyl 6-chloropicolinate → Methyl 6-(2-(7-phenylheptanoyl)oxazol-5-yl)picolinate
Reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[N:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][CH: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.ClC1N=C(C(OC)=O)C=CC=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[N:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][CH:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
Reactant 3
Product 1
Procedure
Methyl 6-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)picolinate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (94 mg, 0.142 mmol) and methyl 6-chloropicolinate following General Procedure A. Flash chromatography (5-10% EtOAc/hexanes) yielded the title compound as a clear oil (72 mg, 100%): 1H NMR (CDCl3, 500 MHz) δ 8.12-8.10 (m, 1H), 7.99 (t, 1H, J=7.8 Hz), 7.90-7.89 (m, 1H), 7.86 (s, 1H), 7.35-7.32 (m, 2H), 7.25-7.22 (m, 3H), 4.94 (t, 1H, J=7.0 Hz), 4.10 (s, 3H), 2.67 (t, 2H, J=7.5 Hz), 2.04-1.96 (m, 2H), 1.74-1.67 (m, 2H), 1.55-1.39 (m, 6H), 0.97 (s, 9H), 0.17 (s, 3H), 0.07 (s, 1H); 13C NMR (CDCl3, 125 MHz) δ 166.5, 165.8, 150.3, 148.7, 148.2, 143.3, 138.4, 128.8, 128.6, 126.8, 126.0, 124.3, 122.5, 69.2, 53.4, 36.8, 36.3, 31.8, 29.6, 26.1, 26.1, 25.5, 14.0, −4.5, −4.7.
Sources & evidence
- ORD record
- ord-eb881047bc144884aba61b51bad6a803
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915270B2
Reaction notes
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