Dimethylamine → HCID 22638755, compound

HRID 1836634Notes

Reaction equation

HRID 1836634 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[CH:6]=[C:5]2[C@@H:22]1[CH2:24][C@H:23]1[CH:25]=O.[CH3:27][NH:28][CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[C:5]2[CH:22]1[CH2:24][CH:23]1[CH2:25][N:28]([CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86587684HCID 86587684, compound

Product 1

HCID 22638755HCID 22638755, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-2-[5,6-difluoro-1-(p-toluenesulfonyl)indol-3-yl]cyclopropane-carboxaldehyde (0.48 g, 1.28 mmol), dimethylamine (3 ml, 6 mmol, 2M/THF) and tetrahydrofuran (15 ml) was treated with sodium triacetoxyborohydride (1.35 g, 6.39 mmol) and stirred at ambient temperature for 1 h. The resulting solution was evaporated in vacuo and the residue treated with 10 N sodium hydroxide (10 ml) and methyl alcohol (10 ml). The solution was heated at a gentle reflux for 2 h then cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 1 N sodium hydroxide, and brine, and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo to an amber colored oil. Silica gel column chromatography (chloroform/2M ammonia in methanol, 9:1) afforded [2-(5,6-difluoro-1H-indol-3-yl)-cyclopropylmethyl]-dimethyl-amine (100 mg, 31%) as a light oil which solidified upon standing. 1H-NMR (400 MHz, CDCl3) 8.09 (1H, br s), 7.40 (1H, m), 7.10 (1H, dd, J=10.6, 6.6), 6.89 (1H, d, J=2.2 Hz), 2.38 (2H, m), 2.34 (6H, s), 1.69 (1H, m), 1.18 (1H, m), 0.90 (1H, m), 0.78 (1H, m).

Workup

  1. customThe resulting solution was evaporated in vacuo
  2. additionthe residue treated with 10 N sodium hydroxide (10 ml) and methyl alcohol (10 ml)
  3. temperatureThe solution was heated at
  4. temperaturea gentle reflux for 2 h
  5. temperaturethen cooled
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with 1 N sodium hydroxide, and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationThe filtrate was concentrated in vacuo to an amber colored oil

Sources & evidence

ORD record
ord-e9c1f1c437814025979e419549de49fb
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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