Potassium Carbonate → 6-(3-Oxo-indan-5-yloxy)-nicotinamide

HRID 747947Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Cl[C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>>[O:11]=[C:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)[CH:10]=2)[CH2:6][CH2:7]1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 804566-Chloronicotinamide

HCID 70206596-Hydroxy-1-indanone

Product 1

HCID 597506386-(3-Oxo-indan-5-yloxy)-nicotinamideYield 38.1%

Procedure

Using a method similar to Intermediate 1, using 6-hydroxy-1-indanone (J. Med. Chem. (1998), 41(7), 1068-1083) (2.07 g, 13.9 mmol), 6-chloronicotinamide (2.08 g, 13.3 mmol) and K2CO3 (2.75 g, 19.9 mmol) gives the title compound (1.36 g) as a yellow solid. Mass spectrum (ion spray): m/z=269 (M+1); 1HNMR (DMSO-d6): 8.57 (s, 1H), 8.26 (d, 1H), 8.02 (s, 1H), 7.63 (d, 1H), 7.46 (m, 2H), 7.33 (s, 1H), 7.14 (d, 1H), 3.10 (t, 2H), 2.68 (t, 2H).

Sources & evidence

ORD record: ord-c717cd4cdcbf43f585a98af73379fa8a
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399774B2

Reaction notes

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