Sodium Carbonate → 1-(3,3-Dimethyl-6-morpholinoindolin-1-yl)ethanone

HRID 1618481Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:15])([CH3:14])[CH2:7][N:8]2[C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br.C([O-])([O-])=O.[Na+].[Na+]>CO.O>[CH3:14][C:6]1([CH3:15])[C:5]2[C:9](=[CH:10][C:2]([N:1]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:3][CH:4]=2)[N:8]([C:11](=[O:13])[CH3:12])[CH2:7]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-(6-amino-3,3-dimethylindolin-1-yl)ethanone (5 g, 24.5 mmol), 1-bromo-2-(2-bromoethoxy)ethane (6.25 g, 26.9 mmol), and Na2CO3 (5.19 g, 49 mmol) in MeOH (25 mL) was heated to 150° C. in a sealed tube. After 2.5 h, the mixture was cooled to rt. The reaction mixture was diluted with water (100 mL). The resulting solid was filtered, washed with water (300 mL), and dried in the air to give 1-(3,3-dimethyl-6-morpholinoindolin-1-yl)ethanone as a grey solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 7.74 (1H, s), 7.06 (1H, d, J=8.1 Hz), 6.61 (1H, dd, J=8.2, 2.1 Hz), 3.82 (2H, s), 3.67-3.76 (4H, m), 2.95-3.06 (4H, m), 2.13 (3H, s), 1.26 (6H, s). Mass Spectrum (ESI) m/e=275.2 (M+1).

Workup

temperaturethe mixture was cooled to rt
filtrationThe resulting solid was filtered
washwashed with water (300 mL)
customdried in the air

Sources & evidence

ORD record: ord-47df8b11681240dd893fff6e39a49713
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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