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

HRID 2364989Notes

Reaction equation

HRID 2364989 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.N[C:12]1[CH:20]=[C:19]2[C:15]([C:16](=CC3NC4CCN(CCN(CC)CC)C(=O)C=4C=3C)[C:17](=[O:21])[NH:18]2)=[CH:14][C:13]=1[F:41].[NH:42]1CCCCC1>O1CCCC1>[F:41][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([NH:42][CH:5]=[O:7])[CH:12]=1)[NH:18][C:17](=[O:21])[CH2:16]2

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8082PiperidineHCID 666072882-(6-Amino-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 59250102N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-formamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of acetic anhydride (1.6 ml) and formic acid (1.2 ml) was stirred for 1 hour at room temperature, and added with 6-amino-5-fluoro-1,3-dihydro-indol-2-one (4.0 g, 24 mmol) obtained from Example 7 in 60 ml of tetrahydrofuran and piperidine (0.04 ml). Upon the completion of the addition, the 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 (4.6 g, 99%) as a white solid.

Workup

  1. additionUpon the completion of the addition
  2. customwas formed
  3. filtrationThe solid was filtered
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0f3e5047f4db43de80c306d10f7e2816
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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