Water → HCID 19360255, compound

HRID 376884Notes

Reaction equation

HRID 376884 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH3:6].[Cl:7][C:8]1[C:13]2[S:14][CH:15]=[C:16]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1.O>CN(C=O)C.C(OCC)(=O)C>[ClH:7].[Cl:7][C:8]1[C:13]2[S:14][CH:15]=[C:16]([N:17]([CH2:4][CH2:5][CH3:6])[C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 19360126HCID 19360126, compound

Product 1

HCID 19360255HCID 19360255, compoundYield 168.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (452 mg, 11.29 mmole, washed with pentane) in dry DMF (15 mL) was added 1-bromopropane (1.03 mL, 11.29 mmole), and thereafter a solution of 7-chloro-3-[(4-pyridinyl)amino]benzo[b]thiophene (2.8 g, 10.75 mmole) in warm DMF (20 mL) was added so that the reaction mixture was warm to the touch. After the addition, the reaction mixture was stirred for two hours, distributed between water and ethyl acetate, and the organic phase was washed with water, dried (MgSO4) and concentrated to afford 3.07 g of a dark brown oil. This was flash chromatographed twice (silica, 5% MeOH/EtOAc then 10% MeOH/EtOAc; alumina, Et2O) to yield 2.36 g of product. The hydrochloride salt was formed in methanol with ethereal hydrogen chloride, the solution was concentrated to a solid and the solid was recrystallized from methanol and diethyl ether. The resulting pale yellow solid was dried for four hours under high vacuum over P2O5 and refluxing toluene to yield 1.77 g, mp 249° C. (dec.).

Workup

  1. temperaturewas warm to the touch
  2. additionAfter the addition
  3. washthe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9220515b66364ea39ae0284c7dfeea71
Source dataset
uspto-grants-2000_02
Patent number
US06022880

Reaction notes

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