1-Bromo-3-chloropropane → HCID 67147656, compound

HRID 490484Notes

Reaction equation

HRID 490484 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]([CH3:13])[CH:7]=[C:6]2[C:14]1[N:22]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[CH:15]=1.[H-].[Na+].Br[CH2:36][CH2:37][CH2:38][Cl:39]>CN(C)C=O.ClCCl.O.C(OC(C)C)(C)C>[Cl:39][CH2:38][CH2:37][CH2:36][O:12][C:11]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]3[N:22]([S:23]([C:26]4[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=4)(=[O:25])=[O:24])[C:17]4=[N:18][CH:19]=[CH:20][CH:21]=[C:16]4[CH:15]=3)=[CH:7][N:8]2[CH3:13])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

8

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 22477326HCID 22477326, compound

Product 1

HCID 67147656HCID 67147656, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 5-methoxy-1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol (0.45 g; 1.006 mmol) in solution in dimethylformamide (5 ml) is placed in a 50 ml round-bottomed flask rendered inert with argon, and sodium hydride (0.06 g; 2.01 mmol) is then added. The reaction mixture becomes dark in color and 1-bromo-3-chloropropane (0.199 ml, 2.01 mmol) is added. The reaction mixture is agitated for 30 minutes at 20° C. The reaction mixture is diluted with dichloromethane (50 ml) and water (100 ml), separated by settling out, and extracted with dichloromethane (2×50 ml). The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure, resulting in an oil. The oil is taken up in diisopropyl ether (10 ml) and then triturated, discarding crystals. After filtration, washing with diisopropyl ether and drying under reduced pressure, 2-[6-(3-chloropropoxy)-5-methoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is isolated in the form of ochre-colored crystals (0.415 g; 79%), the characteristics of which are as follows:

Workup

  1. additionis then added
  2. additionis added
  3. customseparated
  4. extractionextracted with dichloromethane (2×50 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customresulting in an oil
  9. customtriturated
  10. filtrationAfter filtration
  11. washwashing with diisopropyl ether
  12. customdrying under reduced pressure

Sources & evidence

ORD record
ord-05bf2b49876a4b5aa082bdaf18573689
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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