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Carbon tetrabromide → 1-(3-Bromopropyl)-5-methoxy-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 2298773
Notes
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Reaction equation

HRID 2298773 reaction equation
C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:29]([Br:33])(Br)(Br)Br.OC[CH2:36][CH2:37][N:38]1[C:46]2[C:41](=[N:42][C:43]([O:47][CH3:48])=[CH:44][CH:45]=2)[CH2:40][C:39]1=[O:49]>ClCCl>[Br:33][CH2:29][CH2:36][CH2:37][N:38]1[C:46]2[C:41](=[N:42][C:43]([O:47][CH3:48])=[CH:44][CH:45]=2)[CH2:40][C:39]1=[O:49]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 742671,2-Bis(diphenylphosphino)ethaneHCID 113904261-(3-Hydroxypropyl)-5-methoxy-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Product 1

HCID 112661091-(3-Bromopropyl)-5-methoxy-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent
2×

Conditions

Temperature
0 °C

Procedure

Under argon and in an anhydrous medium, 1.50 g (3.76 mmol) of 1,2-bis-diphenylphosphinoethane are added at 0° C. to a solution of 1.25 g (3.76 mmol) of carbon tetrabromide in 20 ml of dichloromethane. After 10 minutes at 0° C., 417 mg (1.88 mmol) of the compound obtained in Step D dissolved in 10 ml of dichloromethane are added to the mixture. The mixture is stirred for 30 minutes at 0° C., and then for 3 hours at room temperature. After hydrolysis of the reaction mixture, the organic phase is dried over magnesium sulphate, filtered and concentrated. Purification by flash chromatography over silica gel (eluant: petroleum ether/ethyl acetate, 8:2) yields the title compound in the form of a white solid.

Workup

  1. additionare added to the mixture
  2. waitfor 3 hours at room temperature
  3. customAfter hydrolysis of the reaction mixture
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography over silica gel (eluant: petroleum ether/ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-561c34b3712944a6a011d11677a3b799
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06495543B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes