Formic Acid → HCID 57479603, compound

HRID 545574Notes

Reaction equation

HRID 545574 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:7][C:6]2=1)#N.C(O)=[O:31]>CO>[F:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:12]1[C:11]2[CH2:10][CH2:9][CH:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[CH2:7][C:6]=2[C:5]2[C:13]1=[CH:14][CH:15]=[C:3]([CH:1]=[O:31])[CH:4]=2

Participants

4

Reactant 2

HCID 284Formic AcidHCID 57431643HCID 57431643, compound

Product 1

HCID 57479603HCID 57479603, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mix N-(6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Preparation 3) (8.1 g, 20.8 mmol), Al—Ni catalyst (15.0 g, 231 mmol) in 90% formic acid (125 mL). Heat at reflux for 3 h, then dilute with MeOH and filter hot. Concentrate and partition the residue between aqueous NaHCO3/EtOAc. Dry the organic layer (MgSO4) and concentrate to give 5.9 g yellow semi-solid. Purify using silica gel chromotagraphy, eluting with 30-75% EtOAc in hexane to give 3.3 g (40%) as a white solid. MS (ES): m/z 393 (M+1), 391 (M−1); HPLC (Method B): Rt=4.41 (100%).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 3 h
  3. filtrationfilter hot
  4. concentrationConcentrate
  5. custompartition the residue between aqueous NaHCO3/EtOAc
  6. dry with materialDry the organic layer (MgSO4)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-e1513c77d68b41c0afe7a4ae22f1f56f
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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