Sodium Bicarbonate → HCID 68279793, compound

HRID 1771067Notes

Reaction equation

HRID 1771067 reaction equation
[CH3:1][C:2]1[N:3]([CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:22][N+:23]([CH3:25])=[CH2:24].[Cl-].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[CH3:22][N:23]([CH2:25][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[C:2]=1[CH3:1])[CH3:24]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 3400031HCID 3400031, compoundHCID 11051579Dimethylmethylenammonium chloride

Product 1

HCID 68279793HCID 68279793, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Methyl 4-((2-methyl-1H-indol-1-yl)methyl)benzoate 3 (0.500 g, 1.90 mmol) and dimethylformiminium chloride (0.200 g, 2.15 mmol) were heated to reflux in a solution of DCM (5 mL) and DMF (2 mL) for 20 h. The reaction was then cooled to RT and DCM (50 mL) was added along with sat. NaHCO3 (20 mL). The organic fraction was isolated and the aqueous solution was further extracted with DCM (2×20 mL). The combined organic fractions were washed with H2O (20 mL), brine (20 mL), dried with Na2SO4 and concentrated in vacuo. The desired product was purified via automated column chromatography method 2 (0.221 g, 37%). 1H NMR (400 MHz, CDCl3): δ 7.94 (d, J=8.1 Hz, 2H), 7.69 (m, 1H), 7.14 (m, 3H), 7.02 (d, J=8.0 Hz, 2H), 5.38 (s, 2H), 3.90 (s, 3H), 3.62 (s, 2H), 2.35 (s, 3H), 2.30 (s, 6H).

Workup

  1. customThe organic fraction was isolated
  2. extractionthe aqueous solution was further extracted with DCM (2×20 mL)
  3. washThe combined organic fractions were washed with H2O (20 mL), brine (20 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe desired product was purified

Sources & evidence

ORD record
ord-01a64e70ff6d4f779b34cca146d374df
Source dataset
uspto-grants-2016_02
Patent number
US09249087B2

Reaction notes

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