Sodium hydride → HCID 22028191, compound

HRID 1791141Notes

Reaction equation

[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[ClH:21].[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][Cl:26]>CN(C=O)C>[ClH:26].[ClH:21].[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][N:12]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:18]2[C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])=[CH:11]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (400 mg, 1.55 mmol) in dry DMF is chilled to 0° C., treated with sodium hydride (60% in oil, 97 mg, 2.43 mmol), stirred for 3 h at 20° C., cooled to −20° C., treated with 2-(dimethylamino)-ethyl chloride hydrochloride (336 mg, 2.33 mmol), stirred at 60° C. for 16 h, cooled to room temperature, quenched with water and extracted with ethyl acetate. The organic extracts are combined, washed with brine, dried over MgSO4 and concentrated in vacuo to afford the free amine of the title compound as a yellowish gum. The gum is dissolved in ethanol, treated with 1N aqueous HCl and concentrated in vacuo. Crystallization of the resultant residue from ethanol/ether affords the title compound as a light tan solid, 111 mg, mp 214–217° C., characterized by mass spectral and HNMR analyses.

Workup

temperaturecooled to −20° C.
stirringstirred at 60° C. for 16 h
temperaturecooled to room temperature
customquenched with water
extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-02a1f083d3dc4686835dfcf7f1f1edb4
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074792B2

Reaction notes

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