Sodium hydride → HCID 57474472, compound

HRID 552973Notes

Reaction equation

[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[Cl:15][CH2:16][CH2:17][CH2:18]I>CN(C=O)C>[Cl:15][CH2:16][CH2:17][CH2:18][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=2)[CH:10]=[CH:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (1.96 g, 49.337 mmol, 60% suspension in mineral oil) was treated with DMF (60 mL), followed by 6-nitroindole (6) (2.0 g, 12.334 mmol) in DMF (20 mL) over a period of 5 min at 0° C. After stirring for 15 min, the solution was treated with 1-chloro-3-iodopropane (3.9 mL, 37.002 mmol), the reaction was brought to room temperature and stirred for 3 h. The reaction was quenched with saturated brine (80 mL), water (80 mL) and cooled to 0° C. The solid was filtered off, washed with water (50-75 mL) and dried to obtain the crude product. The crude product was recrystallised from hot toluene (10 mL)/hexanes (5 mL) to obtain compound 148 (2.637 g, 90%) as solid. mp 85-87° C.; 1H-NMR (CDCl3) δ 2.28-2.36 (m, 2H), 3.46 (t, 2H, J=5.7 Hz), 4.45 (t, 2H, J=6.6 Hz), 6.62 (d, 1H, J=2.7 Hz), 7.43 (d, 1H, J=3.0 Hz), 7.66 (d, 1H, J=8.7 Hz), 8.02 (dd, 1H, J=1.8, 7.9 Hz), 8.36 (d, 1H, J=0.9 Hz).

Workup

customwas brought to room temperature
stirringstirred for 3 h
customThe reaction was quenched with saturated brine (80 mL), water (80 mL)
filtrationThe solid was filtered off
washwashed with water (50-75 mL)
customdried
customto obtain the crude product
customThe crude product was recrystallised from hot toluene (10 mL)/hexanes (5 mL)

Sources & evidence

ORD record: ord-17c9ec6954a542d483b83e620b9fc0c5
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951940B2

Reaction notes

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