Formic Acid → N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-formamide

HRID 2364984Notes

Reaction equation

HRID 2364984 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[CH:13]=[C:14]([F:22])[CH:15]=[C:16]2[C:20]=1[NH:19][C:18](=[O:21])[CH2:17]2>O1CCCC1.N1CCCCC1>[F:22][C:14]1[CH:15]=[C:16]2[C:20](=[C:12]([NH:11][CH:1]=[O:3])[CH:13]=1)[NH:19][C:18](=[O:21])[CH2:17]2

Participants

6

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 592500547-Amino-5-fluoroindolin-2-one

Product 1

HCID 59250102N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-formamideYield 30.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8082PiperidineSolvent

Procedure

A solution of acetic anhydride (0.8 ml) and formic acid (0.6 ml) was stirred for 1 hour at room temperature, and added with 7-amino-5-fluoro-1,3-dihydro-indol-2-one (2.0 g, 12 mmol) obtained from Example 4 in 30 ml of tetrahydrofuran and piperidine (0.02 ml). The resulting mixture was stirred for 3 hours at room temperature until a precipitate was formed. The solid was filtered and recrystallized from methanol to give N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-formamide (700 mg, 30.4%) as a white solid.

Workup

  1. customwas formed
  2. filtrationThe solid was filtered
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-21cb3929b0244beeb2232c261a6f89dd
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

Loading…