Acetic Acid → HCID 22139131, compound

HRID 18231Notes

Reaction equation

HRID 18231 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[CH:12]=O.CN.CO.CC(O)=O.[C:22]([BH3-])#[N:23].[Na+]>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[CH2:12][NH:23][CH3:22]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 6329MethylamineHCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22139131HCID 22139131, compoundYield 52%

Procedure

To 1,3-dimethyl-1H-indole-2-carboxaldehyde (13.0 g, 75 mmole) was added a solution of 2.0 M methylamine in methanol (150 mL, 300 mmole) and HOAc (4.3 mL, 75 mmole). The solution was stirred at RT for 4 hr, then was cooled to 0° C., and sodium cyanoborohydride (5.0 g, 80 mmole) was added portionwise over 5 min. The reaction was then allowed to warm to RT. After 16 hr, the reaction was concentrated under vacuum and the residue was taken up in Et2O. The solution was washed with 1.0 N NaOH then with brine, dried (Na2SO4), and concentrated to dryness. Flash chromatography on silica gel (95:5 CHCl3/methanol containing 5% NH4OH) gave the title compound (7.34 g, 52%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.53 (d, J=7.8 Hz, 1 H), 7.26 (d, J=7.8 Hz, 1H), 7.20 (t, 1 H), 7.09 (t, 1 H), 3.88 (s, 2 H), 3.76 (s, 3 H), 2.46 (s, 3 H), 2.32 (s, 3 H), 1.36 (br s, 1 H).

Workup

  1. temperaturewas cooled to 0° C.
  2. temperatureto warm to RT
  3. waitAfter 16 hr
  4. concentrationthe reaction was concentrated under vacuum
  5. washThe solution was washed with 1.0 N NaOH
  6. dry with materialwith brine, dried (Na2SO4)
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c4394389cfe64bcdb9e19bec26ecd3bb
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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