Toluene → 7-(4-methoxybenzyl)-3-methyl-5-trimethylsilyl-7,9-dihydro-8H-pyrido[4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

HRID 2060909Notes

Reaction equation

ClC1N=[C:4]([NH:18][C:19]2[C:24]([C:25]#[C:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][C:22]([CH3:31])=[CH:21][N:20]=2)[C:5](=[O:17])[N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:7]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:6]2[CH:7]=[C:26]([Si:27]([CH3:30])([CH3:29])[CH3:28])[C:25]3[C:24]4[C:19]([NH:18][C:4]=3[C:5]2=[O:17])=[N:20][CH:21]=[C:22]([CH3:31])[CH:23]=4)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 130 °C

Procedure

In a 2 L round bottom flask, 5-chloro-1-(4-methoxybenzyl)-3-(5-methyl-3-((trimethylsilyl)ethynyl)pyridin-2-ylamino)pyrazin-2(1H)-one (35.2 g, 77.85 mmol) was taken up with anhydrous toluene (880 mL), attached a reflux condenser and transferred to an oil bath that was heated to 130° C. The reaction was stirred in the oil bath for 94 h and concentrated in vacuo to afford a brown solid. The crude was suspended in ethyl acetate (200 mL) and heated to a mild boil. The solids were collected by filtration, washed with additional ethyl acetate, diethyl ether and dried in vacuo to provide the title compound as a pale yellow powder (27.4 g, 89%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.43 (s, 9H) 2.56 (s, 3H) 3.80 (s, 3H) 5.30 (s, 2H) 6.89 (d, J=8.59 Hz, 2H) 7.11 (s, 1H) 7.35 (d, J=8.84 Hz, 2H) 8.22 (s, 1H) 8.52 (d, J=1.52 Hz, 1H). ESI-MS: m/z 392.4 (M+H)+.

Workup

customtransferred to an oil bath
concentrationconcentrated in vacuo
customto afford a brown solid
temperatureheated to a mild boil
filtrationThe solids were collected by filtration
washwashed with additional ethyl acetate, diethyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-5cc2d1d1b9d64cd6884082063bdb74b9
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278450B2

Reaction notes

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