Potassium Carbonate → HCID 59730084, compound

HRID 228426Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=1[CH:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2].Cl[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][N:23]=1.C([O-])([O-])=O.[K+].[K+]>>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][N:23]=2)[C:11]=1[CH:17]([CH3:18])[CH3:19])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 51520946-Chloro-3-pyridinecarbonitrile

HCID 59730111HCID 59730111, compound

Product 1

HCID 59730084HCID 59730084, compoundYield 74.8%

Procedure

Using a method similar to Example 221, Step 1, using [2-(3-hydroxy-2-isopropyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (4.02 g, 14.4 mmol), 6-chloronicotinonitrile (1.99 g, 14.4 mmol) and K2CO3 (2.98 g, 21.5 mmol) gives {2-[3-(5-cyano-pyridin-2-yloxy)-2-isopropyl-phenyl]-ethyl}-carbamic acid tert-butyl ester (4.11 g) as a yellow foam. 1HNMR (CDCl3): 8.50 (s, 1H), 7.92 (d, 1H), 7.17 (t, 1H), 7.06 (d, 1H), 7.01 (d, 1H), 6.86 (d, 1H), 4.63 (br. s, 1H), 3.34 (m, 2H), 3.27 (m, 1H), 2.91 (t, 2H), 1.44 (s, 9H), 1.24 (d, 6H).

Sources & evidence

ORD record: ord-c2a44800ad534883a6636ee1721754fc
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560463B2

Reaction notes

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