Sodium borohydride → HCID 68470494, compound

HRID 506818Notes

Reaction equation

HRID 506818 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[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:34][CH3:35].[BH4-].[Na+]>CO.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[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:34][CH3:35]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 866186352-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde

Product 1

HCID 68470494HCID 68470494, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.9 g of 2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde in 100 cm3 of methanol, at a temperature in the region of 20° C., is added 0.57 g of sodium borohydride. The reaction medium is stirred at room temperature for 3 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 100 cm3 of water and 100 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. 4.92 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methanol are 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-0c9c6ca268fb4bcb96cb6af0e9545d8c
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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