2-Iodoaniline → HCID 16110631, compound

HRID 605632Notes

Reaction equation

HRID 605632 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[NH2:29])=[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.IC1C=CC=CC=1N>>[NH2:29][C:28]1[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=1[C:24]1[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:26][CH:25]=1

Participants

4

Reactant 3

HCID 119952-IodoanilineHCID 16110599HCID 16110599, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110631HCID 16110631, compoundYield 90%

Procedure

2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)aniline. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (188 mg, 0.284 mmol) and 2-iodoaniline following General Procedure A. Flash chromatography (5-20% EtOAc/hexanes) yielded the title compound as a clear oil (122 mg, 90%): 1H NMR (CDCl3, 400 MHz) δ 7.48 (dd, 1H, J=6.4, 9.3 Hz), 7.29-7.25 (m, 2H), 7.21 (s, 1H), 7.18-7.13 (m, 4H), 6.84-6.80 (m, 1H), 6.77-6.75 (m, 1H), 4.85 (t, 1H, J=6.0 Hz), 3.81 (br s, 2H), 2.60 (t, 2H, J=7.5 Hz), 1.97-1.89 (m, 2H), 1.68-1.59 (m, 2H), 1.40-1.29 (m, 6H), 0.91 (s, 9H), 0.11 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 169.1, 155.2, 148.5, 147.9, 134.8, 133.5, 133.4, 132.5, 130.7, 127.8, 123.8, 121.9, 118.4, 73.8, 41.6, 41.1, 36.5, 34.3, 34.3, 30.9, 30.3, 23.3, 0.2, 0.0.

Sources & evidence

ORD record
ord-5c21a730fbd84c54a124621ffbf14085
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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