tert-Butyl Formate → Tert-butyl 4-(5-cyanopyridin-2-yl)piperidine-1-carboxylate

HRID 874949

Reaction equation

HRID 874949 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.I[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.C(OC(C)(C)C)=O>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:3][CH:4]=1)#[N:7]

Participants

4

Reactant 3

HCID 61207tert-Butyl FormateHCID 50057186-Bromopyridine-3-carbonitrileHCID 10892302Tert-butyl 4-iodopiperidine-1-carboxylate

Product 1

HCID 69453251Tert-butyl 4-(5-cyanopyridin-2-yl)piperidine-1-carboxylateYield 27%

Procedure

This compound was synthesized from 6-bromonicotinonitrile and tert-butyl 4-iodopiperidine-1-carboxylate as described for example 49 step 1 (150 mg, yield 27%). 1H NMR (400 MHz, CDCl3) δ 8.82 (d, J=2.0 Hz, 1H), 7.91 (dd, J=8.2 Hz, 2.1 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H), 4.28 (m, 2H), 2.97-2.81 (m, 3H), 1.91 (m, 2H), 1.78-1.67 (m, 2H), 1.48 (s, 9H). MS (ESI) m/z: Calculated for C16H21N3O2: 287.16. found: 188.2 (M+H-Boc)+

Sources & evidence

ORD record
ord-e30fa4a8e33a451eadbef6c90ecba643
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Linked notes

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