Triethylamine → HCID 25003540, compound

HRID 2353451Notes

Reaction equation

HRID 2353451 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:15]([CH3:16])[C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl.C(OCC)(=O)C>[CH3:16][N:15]1[C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:3][CH2:4]3)=[CH:12][CH:13]=[C:14]1[C:17]#[N:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68426072HCID 68426072, compound

Product 1

HCID 25003540HCID 25003540, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile hydrochloride (100 mg, 0.38 mmol) was dissolved in methylene chloride (5 mL) and triethylamine (0.17 mL, 1.14 mmol) was added. The mixture was treated with methanesulfonyl chloride (0.033 mL, 0.42 mmol) and stirred for 3 hours. The mixture was diluted with ethyl acetate, washed with water, 2N HCl, water, brine, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 20-60% ethyl acetate in hexane) to afford 1-methyl-5-[1-(methylsulfonyl)-2,3-dihydro-1H-indol-5-yl]-1H-pyrrole-2-carbonitrile (38 mg). MS (ES) m/z 301.8; HPLC purity 100.0% at 210-370 nm, 8.8 min.; the Xterra® column RP18, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammonium formate buffer pH=3.5 acetonitrile+MeOH) for 10 minutes, hold 4 minutes.

Workup

  1. washwashed with water, 2N HCl, water, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 20-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-39f6632c6dee43a68ef0692f26229d31
Source dataset
uspto-grants-2010_07
Patent number
US07750038B2

Reaction notes

Loading…