Trimethyl orthoformate → HCID 67155774, compound

HRID 2196728Notes

Reaction equation

HRID 2196728 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[C:11]([CH:13]=O)[N:10]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:25][NH:26][CH3:27].COC(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.ClCCCl>[CH3:25][N:26]([CH3:27])[CH2:13][C:11]1[N:10]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2=[N:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]2[CH:12]=1

Participants

9

Reactant 6

HCID 9005Trimethyl orthoformateHCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 73013588HCID 73013588, compound

Product 1

HCID 67155774HCID 67155774, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A round-bottom flask was charged with 5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (0.30 g, 0.91 mmol), dimethylamine hydrochloride salt (0.10 g, 1.27 mmol), trimethoxymethane (0.99 mL, 9.1 mmol), sodium triacetoxyborohydride (0.25 g, 1.18 mmol), sodium acetate (0.10 g, 1.27 mmol) and 1,2-dichloroethane (9.0 mL). The mixture was stirred at room temperature for 24 hours, after which saturated aqueous sodium bicarbonate was added, then dichloromethane. The layers were separated. The aqueous layer was extracted twice with dichloromethane. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography to afford N,N-dimethyl-1-(5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanamine (0.16 g, 49%).

Workup

  1. customThe layers were separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. dry with materialThe organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-1ca7fadad1af42a789eaa4e50e295f11
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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