Sodium cyanoborohydride → HCID 67224209, compound

HRID 1968183Notes

Reaction equation

HRID 1968183 reaction equation
[NH2:1][CH:2]([CH:6]1[CH2:8][CH2:7]1)[CH2:3][CH2:4][OH:5].[CH:9]([C:11]1[C:19]2[C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:16]=[N:15][C:14]=2[N:13]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:12]=1)=O.C([BH3-])#N.[Na+]>CO.CC(O)=O>[CH:6]1([CH:2]([NH:1][CH2:9][C:11]2[C:19]3[C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:16]=[N:15][C:14]=3[N:13]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:12]=2)[CH2:3][CH2:4][OH:5])[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 24729719HCID 24729719, compoundHCID 58293521HCID 58293521, compound

Product 1

HCID 67224209HCID 67224209, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

3-Amino-3-cyclopropylpropan-1-ol (30 mg, 0.26 mmol) was added to a solution of 1-tert-butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (39.6 mg, 0.13 mmol) in MeOH (3 mL) with AcOH (2 drops). After stirring for 90 min at rt, sodium cyanoborohydride (33 mg, 0.53 mmol) was added, and the reaction was stirred for an additional 3 h. The mixture was quenched with sat. NaHCO3 solution and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated in vacuo to give 50 mg of crude 1-tert-butyl 4-methyl 3-((1-cyclopropyl-3-hydroxypropylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate as a yellow oil which was used without further purification. [M+H] found 404.

Workup

  1. stirringthe reaction was stirred for an additional 3 h
  2. customThe mixture was quenched with sat. NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccb86139417e4ba08bef49ba421dcd0b
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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