Water → N,N-diethyl-5-(1-methyl-1H-indol-2-yl)pyridine-3-sulfonamide

HRID 1661736Notes

Reaction equation

HRID 1661736 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1B(O)O.Br[C:15]1[CH:16]=[C:17]([S:21]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])(=[O:23])=[O:22])[CH:18]=[N:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.O1CCOCC1>[CH2:27]([N:24]([CH2:25][CH3:26])[S:21]([C:17]1[CH:18]=[N:19][CH:20]=[C:15]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:16]=1)(=[O:22])=[O:23])[CH3:28]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 198548155-Bromo-N,N-diethylpyridine-3-sulfonamideHCID 22733820(1-Methyl-1H-indol-2-yl)boronic acid

Product 1

HCID 58215618N,N-diethyl-5-(1-methyl-1H-indol-2-yl)pyridine-3-sulfonamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A flask is charged with 1-methyl-1H-indol-2-ylboronic acid (90 mg, 0.512 mmol), 5-bromo-N,N-diethylpyridine-3-sulfonamide (100 mg, 0.341 mmol) and polymer supported Pd(PPh3)4 (189 mg, 0.017 mmol), and the flask is flushed with N2 for 5 min. 1,4-Dioxane (10 mL) and 2M K2CO3 in water (0.512 mL, 1.023 mmol) are added under N2 and the mixture is stirred at 90° C. under N2 for 2 h. The mixture is then cooled to room temperature and DMF (4 mL) is added. The mixture is concentrated in vacuo and the residue is filtered and the filtrate is purified by Xterra RP18 eluting with a 1:9 to 9:1 acetonitrile-water gradient to give N,N-diethyl-5-(1-methyl-1H-indol-2-yl)pyridine-3-sulfonamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.1 Hz, 6H), 3.29 (d, J=7.1 Hz, 4H), 3.80 (s, 3H), 6.85 (s, 1H), 7.08-7.14 (m, 1H), 7.26 (td, J=7.71, 1.26 Hz, 1H), 7.56 (dd, J=8.3, 0.5 Hz, 1H), 7.63 (d, J=7.8 Hz, 1H), 8.33 (t, J=2.1 Hz, 1H), 9.00 (d, J=2.0 Hz, 1H), 9.10 (d, J=2.2 Hz, 1H). HRMS: (ESI) m/z 344.1428 [(M+H)+ Calcd for C18H22N3O2S 344.1427].

Workup

  1. customthe flask is flushed with N2 for 5 min
  2. temperatureThe mixture is then cooled to room temperature
  3. concentrationThe mixture is concentrated in vacuo
  4. filtrationthe residue is filtered
  5. customthe filtrate is purified by Xterra
  6. washRP18 eluting with a 1:9 to 9:1 acetonitrile-water gradient

Sources & evidence

ORD record
ord-dd19d550f666465cb4b3bf29b11a5606
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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