2-Chloro-4-(trifluoromethyl)pyridine → HCID 16110710, compound

HRID 605656Notes

Reaction equation

HRID 605656 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[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=C(C(F)(F)F)C=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:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[CH:29][N: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 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 16110620HCID 16110620, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110710HCID 16110710, compoundYield 77%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-(trifluoromethyl)pyridin-2-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (130 mg, 0.196 mmol) and 2-chloro-4-(trifluoromethyl)pyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (80 mg, 77%): 1H NMR (CDCl3, 400 MHz) δ 8.79 (d, 1H, J=5.0 Hz), 7.84 (s, 1H), 7.73 (s, 1H), 7.43 (dd, 1H, J=5.0, 0.9 Hz), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 4.88 (dd, 1H, J=7.3, 5.9 Hz), 2.60 (t, 2H, J=7.8 Hz), 1.93 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.91 (s, 9H), 0.11 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.5, 150.9, 149.6, 148.6, 142.8, 139.3 (q, J=33.9 Hz), 128.4, 128.2, 126.6, 125.6, 118.1 (q, J=3.5 Hz), 114.6 (q, J=3.0 Hz), 68.7, 36.4, 35.9, 31.4, 29.1, 25.7, 25.7, 18.2, −5.0, −5.1.

Sources & evidence

ORD record
ord-c0206303d1b848abb1890f6c4770ccd3
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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