4-Bromo-2-fluorobenzonitrile → Tert-butyl 4-[5-(4-cyano-3-fluorophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylate

HRID 710132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710132
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[N:14][C:13]=3[CH:30]=2)O1.Br[C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[C:35]([F:41])[CH:34]=1>>[C:37]([C:36]1[CH:39]=[CH:40][C:33]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]4)=[N:14][C:13]=3[CH:30]=2)=[CH:34][C:35]=1[F:41])#[N:38]

Komponenten

3

Edukt 2

HCID 7360294-Bromo-2-fluorobenzonitrileHCID 71090269Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-yl)piperidine-1-carboxylate

Produkt 1

HCID 71114207Tert-butyl 4-[5-(4-cyano-3-fluorophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylateAusbeute 47,5 %

Versuchsvorschrift

Following the General Procedure-2, the titled compound (70 mg) was prepared from Intermediate 8 (150 mg, 0.35 mmol) and 4-bromo-2-fluorobenzonitrile (70 mg, 0.35 mmol) as a white solid. M.P.: 138-142° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.87 (d, J 1.6, 1H), 7.72-7.68 (m, 1H), 7.59 (d, J 8.5, 1H), 7.53-7.42 (m, 3H), 4.15 (d, J 10.6, 2H), 3.20-3.11 (m, 1H), 3.00 (t, J 11.8, 2H), 2.2-2.12 (m, 2H), 1.98-1.86 (m, 2H), 1.56 (S, 9H).

Quellen und Nachweise

ORD-Eintrag
ord-2675565f0ff2401089426b3afee9dfdd
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181214B2

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