Sodium borohydride → HCID 68466964, compound

HRID 506803Notes

Reaction equation

HRID 506803 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[NH:23][C:16]4[N:17]=[CH:18][CH:19]=[C:20]([CH:21]=[O:22])[C:15]=4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:24][CH3:25].[BH4-].[Na+]>CO.ClCCl.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[NH:23][C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][OH:22])=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:24][CH3:25]

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 866186362-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde

Product 1

HCID 68466964HCID 68466964, compoundYield 63.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.07 g of 2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde in 7 cm3 of methanol and 20 cm3 of dichloromethane, at a temperature in the region of 20° C., is added 0.012 g of sodium borohydride. The reaction medium is stirred at room temperature for 24 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 10 cm3 of water and 20 cm3 of ethyl acetate. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.045 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methanol is obtained 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-13661a55121f4c3799ab883a09961f80
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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