Potassium Carbonate → HCID 22461262, compound

HRID 1937625Notes

Reaction equation

HRID 1937625 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=2[C:4](=[O:13])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].Cl[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1>CN(C=O)C.[Cu]Br>[CH2:11]([C:6]1[C:5]2[C:4](=[O:13])[CH2:3][C:2]([CH3:1])([CH3:14])[CH2:10][C:9]=2[N:8]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:7]=1)[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-Chloropyrimidine2×HCID 22461260HCID 22461260, compound

Product 1

HCID 22461262HCID 22461262, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 6,6-dimethyl-3-ethyl-4,5,6,7-tetrahydro-1H-indole-4-one (100 mg, 0.52 mmol), K2CO3 (87 mg, 0.63 mmol), copper (I) bromide (15 mg, 0.1 mmol) and 2-chloropyrimidine (71 mg, 0.63 mmol) in DMF (1 mL) were heated at 180° C. for 24 h. More copper (I) bromide (16 mg, 0.1 mmol) and 2-chloropyrimidine (50 mg) were added and heating continued for a further 24 h. The DMF was evaporated and the residue partitioned between water and DCM. The organic layer was separated and the aqueous phase extracted with DCM (2×). The combined organic layers were washed with water, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel, eluting with 4:1 isohexane: EtOAc, to afford the title compound (35 mg, 25%) as a yellow solid. mp 111-114° C. Found: C, 71.07; H, 6.98; N, 15.20%. Calc C16H19N3O: C, 71.35; H, 7.11; N, 15.60%. 1H NMR (360 MHz, d6-DMSO) δ 1.06 (6H,s), 1.15 (3H,t, J=7.4 Hz), 2.30 (2H,s), 2.67 (2H,q, J=7.3 Hz), 3.23 (2H,s), 7.44 (1H,t, J=4.8Hz), 7.47 (1H,s), 8.86 (2H,d, J=4.8Hz). MS (ES+) 270 (+1).

Workup

  1. temperatureheating
  2. customThe DMF was evaporated
  3. customthe residue partitioned between water and DCM
  4. customThe organic layer was separated
  5. extractionthe aqueous phase extracted with DCM (2×)
  6. washThe combined organic layers were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washeluting with 4:1 isohexane

Sources & evidence

ORD record
ord-3655262aafd0480f955f27717bbd1ddf
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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