Formic Acid → HCID 86761720, compound

HRID 2191436Notes

Reaction equation

HRID 2191436 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.N1CCCCC1>O1CCCC1>[F:22][C:14]1[CH:13]=[C:12]([NH:11][CH:1]=[O:3])[C:20]2[C:16](=[CH:17][C:18](=[O:21])[N:19]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8082PiperidineHCID 592500547-Amino-5-fluoroindolin-2-one

Product 1

HCID 86761720HCID 86761720, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture 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 20b (2.0 g, 12 mmol) in 30 ml of tetrahydrofuran to the above mixture, followed by piperidine (0.02 ml). The resulting mixture was stirred for 3 hours until precipitates were formed, filtered to provide the crude product (1.95 g), and recrystallized from methanol to obtain the title compound 5-fluoro-7-formamido-indol-2-one 20c (700 mg, yield 30.4%) as a white solid.

Workup

  1. stirringThe resulting mixture was stirred for 3 hours
  2. customuntil precipitates
  3. customwere formed
  4. filtrationfiltered
  5. customto provide the crude product (1.95 g)
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8fdcc64bd5b546cd9fc5527433bb23d3
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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