Formic Acid → HCID 59425713, compound

HRID 1009564Notes

Reaction equation

HRID 1009564 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) are heated at 65° C. for 1 hour. This is 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, is taken up in THF (1.2 mL) and added to the formic acetic anhydride mixture. This is stirred at 0° C. for 30 minutes. The reaction mixture is then partitioned between H2O and EtOAc. The EtOAc layer is washed with saturated NaHCO3, followed by saturated brine. The organic layer is dried and concentrated. Purification by silica gel chromatography (4/1, CH2Cl2/EtOAc) yields 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 is then partitioned between H2O and EtOAc
  2. washThe EtOAc layer is washed with saturated NaHCO3
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (4/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-ea3b16cf94004a7799b4dffd0ee8a88e
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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