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Sodium Hydroxide → HCID 68471024, compound

HRID 506817
Notes
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Reaction equation

HRID 506817 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[NH:30][C:16]4=[N:17][CH:18]=[CH:19][C:20](/[CH:21]=[N:22]/[C:23]5[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=5)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:31][CH3:32].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.O.ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[NH:30][C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH:22][C:23]5[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=5)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:31][CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 178486707HCID 178486707, compound

Product 1

HCID 68471024HCID 68471024, compoundYield 46.8%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalyst
HCID 887
Methanol
Solvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.085 g of 4-{[1-[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]meth-(E)-ylidene]amino}phenol in 20 cm3 of methanol, at a temperature in the region of 20° C., are added 0.013 g of zinc chloride and 0.013 g of sodium cyanoborohydride. The reaction medium is stirred at the same temperature for 4 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 10 cm3 of water and 25 cm3 of dichloromethane, and then basified with 0.1N sodium hydroxide. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure to give 0.04 g of 4-{[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]amino}phenol with the following characteristics:

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. customThe residue obtained
  3. customAfter separation of the phases
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b762409912c4d42a781f5cbb1871623
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786114B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes