Methanol → HCID 22100881, compound

HRID 1458342Notes

Reaction equation

HRID 1458342 reaction equation
B.C1COCC1.[CH3:7][C:8]1[CH:9]=[C:10]([C:15]2[NH:16][C:17]3[C:22]([C:23]=2[CH2:24][CH2:25][NH:26][C:27](=O)[CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:21][C:20]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][CH:18]=3)[CH:11]=[C:12]([CH3:14])[CH:13]=1.CO.CN(C)CCO>O1CCCC1>[CH3:14][C:12]1[CH:11]=[C:10]([C:15]2[NH:16][C:17]3[C:22]([C:23]=2[CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:21][C:20]([S:38]([CH3:41])(=[O:39])=[O:40])=[CH:19][CH:18]=3)[CH:9]=[C:8]([CH3:7])[CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 79022-(Dimethylamino)ethanolHCID 2723981Borane;tetrahydrofuranHCID 22100889HCID 22100889, compound

Product 1

HCID 22100881HCID 22100881, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Borane-THF ((1.0M soln in tetrahydrofuran, 27 mL) was added dropwise to a solution of N-[2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]ethyl]-4-pyridin-4-yl-butyramide (1.45 g, 2.96 mmol) in dry tetrahydrofuran (20 mL), and the solution was heated at reflux for 2 hours. At this time, methanol was added to quench excess borane, and the resulting solution was evaporated to dryness. The residue was dissolved in tetrahydrofuran (20 mL), and N,N-dimethylethanolamine (8.9 mL, 88.86 mmol) was added. The solution was heated at reflux for 2.5 hr and then concentrated to dryness. The crude material was purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (1.0 g, 71%). m/e=476 (M+H)

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 hours
  3. customto quench excess borane
  4. customthe resulting solution was evaporated to dryness
  5. dissolutionThe residue was dissolved in tetrahydrofuran (20 mL)
  6. temperatureThe solution was heated
  7. temperatureat reflux for 2.5 hr
  8. concentrationconcentrated to dryness
  9. customThe crude material was purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-8403085bb8534a2194856db149d92165
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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