Methyl 5-bromothiophene-2-carboxylate → Methyl 5-(2-(7-phenylheptanoyl)oxazol-5-yl)thiophene-2-carboxylate

HRID 605665Notes

Reaction equation

HRID 605665 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[S:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[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.BrC1SC(C(OC)=O)=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[S:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 16110629HCID 16110629, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110718Methyl 5-(2-(7-phenylheptanoyl)oxazol-5-yl)thiophene-2-carboxylateYield 94%

Procedure

Methyl 5-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)thiophene-2-carboxylate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (89 mg, 0.134 mmol) and methyl 5-bromothiophene-2-carboxylate following General Procedure A. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (65 mg, 94%): 1H NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J=3.6 Hz), 7.26-7.23 (m, 4H), 7.17-7.14 (m, 3H), 4.80 (t, 1H, J=6.0 Hz), 3.89 (s, 3H), 2.58 (t, 2H, J=7.6 Hz), 1.95-1.87 (m, 2H), 1.68-1.56 (m, 2H), 1.38-1.27 (m, 6H), 0.88 (s, 9H), 0.09 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 167.4, 150.8, 147.9, 141.3, 139.2, 137.7, 133.5, 133.3, 130.7, 129.2, 129.2, 128.5, 73.7, 57.5, 41.4, 41.0, 36.5, 34.2, 30.8, 30.9, 30.2, 23.3, 0.2, 0.0.

Sources & evidence

ORD record
ord-60efb91dd61a40a69f2ec9b3741b269e
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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