Pyridine → HCID 21071920, compound

HRID 1372428Notes

Reaction equation

HRID 1372428 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl[S:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH2:18]2)(=[O:14])=[O:13].N1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:12]([C:15]1[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH2:18]3)(=[O:13])=[O:14])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 27744635-FluoroindolineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 21071920HCID 21071920, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-fluoroindoline from above, 5-chlorosulfonyl-2-oxindole (6.1 g, 1.2 equivalent) and pyridine (7.1 mL) in dichloromethane (40 mL) was stirred at room temperature overnight. The reaction was concentrated and the residue was recrystallized from methanol to give 5 g (68% yield) of 5-(5-fluoro-2,3-dihydro-indole-1-sulfonyl)-1,3-dihydro-indol-2-one as a pink-colored solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.75 (br s, 1H, NH), 7.60 (m, 2H), 7.60 (dd, 1H), 7.02 (m, 2H), 6.90 (d, 1H), 3.89 (t, 2H, CH2), 3.52 (s, 2H, CH2), 2.87 (t, 2H, CH2). MS 331 [M+−1].

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-bf6ba1ca727348cb82481cf8b85c6866
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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