Triethylamine → 445441-27-0

HRID 1766268Notes

Reaction equation

HRID 1766268 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([OH:23])=[CH:20][CH:21]=2)[C:16]([CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:15]1.C(N(CC)CC)C.[C:38]([O-:41])([OH:40])=O.[Na+]>C(Cl)Cl.O1CCCC1.CN(C=O)C.O.C(OCC)(=O)C>[C:19]([OH:23])(=[O:10])[C:38]([OH:41])=[O:40].[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:23][S:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])(=[O:11])=[O:10])=[CH:20][CH:21]=2)[C:16]([CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:15]1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 179801241-Methyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-ol

Product 1

HCID 24880040445441-27-0

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,6-difluorobenzenesulfonyl chloride (312 mg, 1.47 mmol) in methylene chloride (2 mL) was added to a solution of 1-methyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (327 mg, 1.34 mmol) and triethylamine (226 μL, 1.6 mmol) in tetrahydrofuran (10 mL), methylene chloride (2 mL) and DMF (6 mL). The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with water and ethyl acetate, basified with saturated NaHCO3, and extracted with ethyl acetate. The ethyl acetate extracts were washed with water, brine, dried (NaSO4), filtered and concentrated under reduced pressure to give 550 mg of a white solid. The product was purified by flash chromatography (silica gel, 5%,10% 2M ammonia in methanol/methylene chloride) to give 440 mg (78%) of homogeneous title compound as a white foam. The product was crystallized as the oxalic acid salt from ethyl acetate to give a white powder: mp=195-198° C. dec; MS(m/e): 421 (M+1); Calculated for C23H22F2N2O3S.C2H2O4: C, 54.11; H, 4.74; N, 5.49. Found: C, 53.86; H, 4.62; N, 5.29.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with water, brine
  3. dry with materialdried (NaSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-138d9481a45d42c696d5bfc47b391bf5
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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