Dimethylamine → HCID 57803393, compound

HRID 1173223Notes

Reaction equation

HRID 1173223 reaction equation
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1.[BH4-].[Na+]>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Br:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][N:2]([CH3:3])[CH3:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 4311764Sodium borohydrideHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 57803393HCID 57803393, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of titanium tetraisopropoxide (6.4 g, 22 mmol) and 2.0 M of dimethylamine in methanol (22 mL, 44 mmol), 6-bromo-pyridine-3-carbaldehyde (2.10 g, 11 mmol) in 20 mL of methanol was added. After being stirred at r.t. for 5 hrs, sodium borohydride (0.43 g, 11 mmol) was added and the mixture was stirred overnight. The reaction was quenched by addition of 10 mL of water and extracted twice using EtOAc. The combined extracts were dried and concentrated. After flash column using 20-40% methanol in EtOAc and 0.5% NH4OH, 1.15 g of oil was obtained (47% yield), MS: 214.0, 216.0 (M++1).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction was quenched by addition of 10 mL of water
  3. extractionextracted twice using EtOAc
  4. customThe combined extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a84190c7d96b402c8cd9e1fd87ef2e79
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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