Pyridine → HCID 57795601, compound

HRID 2099554Notes

Reaction equation

HRID 2099554 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].N1C=CC=CC=1.[O:11]=[C:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=2)[NH:13]1>>[CH:2]([O:4][S:21]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:11])[CH2:20]2)(=[O:22])=[O:23])([CH3:3])[CH3:1]

Participants

4

Reactant 3

HCID 1049PyridineHCID 3776IsopropanolHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 57795601HCID 57795601, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 2-propanol (1.8 mL, 23.8 mmol) and pyridine (7.0 mL, 86.4 mmol) at 0° C. was added 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride (5.0 g, 21.6 mmol) in one portion. The resulting suspension was stirred at 0° C. for 45 mins and then warmed RT for 1 h. The reaction mixture was partitioned between DCM and 1M HCl. The organic layer was washed successively with 50 mL of 1M HCl, water, and brine. The organic layers were dried over MgSO4 and concentrated to produce an orange solid. Yield: 4.06 g (74%). 1H-NMR (400 MHz, DMSO-d6): δ 10.90 (s, 1H), 7.74 (dd, J=8.2, 1.9 Hz, 1H), 7.70 (s, 1H), 7.01 (d, J=8.2 Hz, 1H), 4.68-4.58 (m, 1H), 3.75-3.69 (m, 2H), 1.19 (d, J=6.2 Hz, 6H). LC/MS (10-99%): M/Z: M+(obs) 256.1; tR=2.10 min.

Workup

  1. temperaturewarmed RT for 1 h
  2. customThe reaction mixture was partitioned between DCM and 1M HCl
  3. washThe organic layer was washed successively with 50 mL of 1M HCl, water, and brine
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customto produce an orange solid

Sources & evidence

ORD record
ord-ac9ea0eef6fc4a4bbf6ca2c51a711d8a
Source dataset
uspto-grants-2009_08
Patent number
US07569604B2

Reaction notes

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