Cesium carbonate → HCID 58574870, compound

HRID 1619429Notes

Reaction equation

HRID 1619429 reaction equation
Br[C:2]1[CH:17]=[CH:16][N:5]2[C:6](=[O:15])[C:7]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:8]=3[N:9]=[C:4]2[CH:3]=1.[C:18]1([C:24]2[N:25]=[CH:26][NH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.[Cu]I>[C:18]1([C:24]2[N:25]=[CH:26][N:27]([C:2]3[CH:17]=[CH:16][N:5]4[C:6](=[O:15])[C:7]5[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:8]=5[N:9]=[C:4]4[CH:3]=3)[CH:28]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 58574318HCID 58574318, compoundHCID 178418822HCID 178418822, compound

Product 1

HCID 58574870HCID 58574870, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-7,8,9,10-tetrahydrocyclohepta[d]pyrido[1,2-a]pyrimidin-11(6H)-one (50 mg, 0.17 mmol), 4-phenyl-1H-imidazole (37.4 mg, 0.26 mmol), CuI (8 mg, 0.04 mmol) and Cs2CO3 in DMF was stirred at 80° C. under nitrogen. The completion of the reaction was monitored by TLC. After the suspension was diluted with water (30 mL) and extracted with ethyl acetate (3×50 mL), the combined organic phases were concentrated to crude product and 23 mg desired product was obtained by column chromatography purification. MS (ESI): 357 (MH+); MS (ESI): 357 (MH+); 1H NMR (300 MHz, CDCl3) δ 9.15-9.13 (d, J=7.83 Hz, 1H), 8.16 (s, 1H), 7.87-7.85 (d, J=7.38 Hz, 2H), 7.72 (s, 1H), 7.57-7.56 (d, J=2.19 Hz, 1H), 7.48-7.44 (t, J=7.35 Hz, 2H), 7.38-7.35 (d, J=7.08 Hz, 1H), 7.26 (m, 1H), 3.00-2.97 (m, 4H), 1.93-1.91 (m, 2H), 1.79-1.77 (m, 2H), 1.71-1.69 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. concentrationthe combined organic phases were concentrated to crude product

Sources & evidence

ORD record
ord-c92bca0b1a814acbafd6a6db3e25d301
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…