Potassium Carbonate → 6-(1-Oxo-indan-5-yloxy)-nicotinamide

HRID 747945Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.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:7]1[C:8]2[C: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][CH:9]=2)[CH2:5][CH2:6]1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 804566-Chloronicotinamide

HCID 2331475-Hydroxy-1-indanone

Product 1

HCID 597506396-(1-Oxo-indan-5-yloxy)-nicotinamideYield 47.2%

Procedure

Using a method similar to Intermediate 1, using 5-hydroxy-1-indanone (2.44 g, 16.5 mmol), 6-chloronicotinamide (2.34 g, 15.0 mmol) and K2CO3 (3.11 g, 22.5 mmol) gives the title compound (1.90 g) as a yellow solid. Mass spectrum (ion spray): m/z=269 (M+1); 1HNMR (DMSO-d6): 8.63 (s, 1H), 8.30 (d, 1H), 8.06 (s, 1H), 7.68 (d, 1H), 7.52 (s, 1H), 7.33 (s, 1H), 7.19 (d, 1H), 7.17 (d, 1H), 3.07 (t, 2H), 2.64 (t, 2H).

Sources & evidence

ORD record: ord-c68061670a6e4e7eabf22adef379a01a
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399774B2

Reaction notes

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