Formic Acid → HCID 59426129, compound

HRID 907167Notes

Reaction equation

C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[NH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]([CH2:34][CH3:35])[C:23]3[C:28]([C:29]=2[C:30]#[N:31])=[CH:27][CH:26]=[C:25]([O:32][CH3:33])[CH:24]=3)=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[C:30]([C:29]1[C:28]2[C:23](=[CH:24][C:25]([O:32][CH3:33])=[CH:26][CH:27]=2)[N:22]([CH2:34][CH3:35])[C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][NH:11][CH:8]=[O:10])=[CH:16][CH:17]=1)#[N:31]

Participants

Conditions

Temperature: 0 °C

Procedure

Acetic anhydride (700 μL) and 98% formic acid (280 μL) were heated at 65° C. for 1 h. This was cooled to 0° C. 2-[4-(2-Aminoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (30 mg, 0.09 mmol), prepared as in example 1BB, was taken up in THF (400 μL), and added to the mixed anhydride. This was stirred at 0° C. for 45 minutes. The mixture was then portioned between EtOAc and aqueous NaHCO3. The organic layer was dried and concentrated. Purification by silica gel chromatography (4/1, CH2Cl2/acetone) yielded N-{2-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)phenoxy]-ethyl} formamide (28 mg, 86%) as a white solid.

Workup

customThe organic layer was dried
concentrationconcentrated
customPurification by silica gel chromatography (4/1, CH2Cl2/acetone)

Sources & evidence

ORD record: ord-73791e7da1de4b2693d313064056fa4a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013006B2

Reaction notes

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