Dimethylamine → HCID 10015826, compound

HRID 2212981Notes

Reaction equation

HRID 2212981 reaction equation
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[NH:10][CH:9]=1)=O.CO.[CH3:21][NH:22][CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:21][N:22]([CH2:1][C@@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[NH:10][CH:9]=1)[CH3:23]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 86591644HCID 86591644, compound

Product 1

HCID 10015826HCID 10015826, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trans-3-(2-formyl-cyclopentyl)-1H-indole-5-carbonitrile (200 mg, 0.84 mMol) was stirred in THF (5 mL) and methanol (30 mL) with dimethylamine (0.84 mL, 2M in THF, 1.68 mMol) for 5 min. Sodium triacetoxyborohydride (530 mg, 2.52 mMol) was added and the reaction was stirred a further 30 min. The solvent was evaporated in vacuo and the residue was dissolved in 1N sodium hydroxide (20 mL). The reaction was extracted with ethyl acetate (3×10 mL), dried with magnesium sulfate, and evaporated to a white powder. The material was purified by precipitation from hot methylene chloride to provide the product (144 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.32 (1H, brs), 8.00 (1H, s), 7.39 (2H, m), 7.12 (1H, d, J=1.8 Hz), 2.90 (1H, m), 2.17 (6H, s), 2.06–2.33 (5H, m), 1.66–1.90 (3H, m), 1.49 (1H, m); MS m/e 268.2 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in 1N sodium hydroxide (20 mL)
  3. extractionThe reaction was extracted with ethyl acetate (3×10 mL)
  4. dry with materialdried with magnesium sulfate
  5. customevaporated to a white powder
  6. customThe material was purified by precipitation from hot methylene chloride

Sources & evidence

ORD record
ord-7cbe5f1115714156b128f144e6118616
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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