Formic Acid → HCID 59425713, compound

HRID 907134Notes

Reaction equation

HRID 907134 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2[N:21]([CH2:33][CH3:34])[C:22]3[C:27]([C:28]=2[C:29]#[N:30])=[CH:26][CH:25]=[C:24]([O:31][CH3:32])[CH:23]=3)=[CH:14][CH:13]=1.C(OC=O)(=O)C>C1COCC1>[C:29]([C:28]1[C:27]2[C:22](=[CH:23][C:24]([O:31][CH3:32])=[CH:25][CH:26]=2)[N:21]([CH2:33][CH3:34])[C:20]=1[C:19]#[C:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][CH:8]=[O:10])=[CH:13][CH:14]=1)#[N:30]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 75269Acetic-formic anhydrideHCID 11587731HCID 11587731, compound

Product 1

HCID 59425713HCID 59425713, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Acetic anhydride (2.5 mL) and 98% formic acid (1.0 mL) were heated at 65° C. for 1 hour. This was cooled to 0° C. 2-(4-Aminophenylethynyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.32 mmol), prepared as in example 1H, was taken up in THF (1.2 mL) and added to the formic acetic anhydride mixture. This was stirred at 0° C. for 30 minutes. The reaction mixture was then partitioned between H2O and EtOAc. The EtOAc layer was washed with saturated NaHCO3, followed by saturated brine. The organic layer was dried and concentrated. Purification by silica gel chromatography (4/1, CH2Cl2/EtOAc) yielded of N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-formamide (105 mg, 96%) as a yellow solid.

Workup

  1. customThe reaction mixture was then partitioned between H2O and EtOAc
  2. washThe EtOAc layer was washed with saturated NaHCO3
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (4/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-a6bdb11861b546348e84576fec6a7938
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…