Sodium hydride → HCID 70583868, compound

HRID 1477892Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[CH:20]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:9])([CH3:6])([CH3:5])[CH3:4].[F:32][CH2:33][CH2:34]I>CN(C=O)C>[C:3]([O:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[C:20]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:34][CH2:33][F:32])[C:21]([O:23][CH3:24])=[O:22])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of NaH (60% dispersion in mineral oil) (22 mg, 0.55 mmol) in anhydrous DMF (3 mL) under nitrogen atmosphere was added methyl 2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)acetate (207 mg, 0.5 mmol), as described in Example 2 step B, in anhydrous DMF (2 mL) and the mixture was then stirred at 0° C. for 1 h. To this mixture was added 1-fluoro-2-iodoethane (17.4 mg, 1 mmol), and the mixture was then stirred at room temperature for 4 h. The volatile was evaporated. The residue was purified by silica gel chromatography eluting with PE/EA (10/1 to 3/1, v/v) to afford the title compound as a white solid. LC/MS m/z=405.1[M+H]+.

Workup

stirringthe mixture was then stirred at room temperature for 4 h
customThe volatile was evaporated
customThe residue was purified by silica gel chromatography
washeluting with PE/EA (10/1 to 3/1

Sources & evidence

ORD record: ord-efdf7d4ad4d54eedb9c64c3e2ca5fa82
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403807B2

Reaction notes

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