Pyridine → HCID 18932905, compound

HRID 1597953Notes

Reaction equation

HRID 1597953 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=2)[CH2:17][CH2:16]1.Br[CH2:26][CH2:27][CH2:28][CH2:29]Br.N1C=CC=CC=1>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:22]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 80561,4-DibromobutaneHCID 54313644HCID 54313644, compound

Product 1

HCID 18932905HCID 18932905, compoundYield 16.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

To 1-(6,7-dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-6-ylamine (103 mg, 0.320 mmol; from Example 30) in DMF (4 mL) was added 1,4-dibromo-butane (42 μL, 0.352 mmol) and pyridine (34 μL, 0.64 mmol) and the mixture was heated to 110° C. for 36 hours under N2(g). The mixture was diluted with saturated aqueous NaHCO3 and extracted with EtOAc/Et2O (1:1) and the organic phase was washed with water and brine, dried over Na2SO4(s), filtered and concentrated in vacuo. The residue was chromatographed on silica (4% MeOH/CHCl3) to afford 20 mg of product. (M.P. 198°-205° C. (dec); GC-MS: 376 (M+); anal. RP18-HPLC RT: 5.05 min.).

Workup

  1. extractionextracted with EtOAc/Et2O (1:1)
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica (4% MeOH/CHCl3)

Sources & evidence

ORD record
ord-e1a0bdb884de4813a4ede4beeec36d60
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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