1-Benzyl-5-chloro-3-(5-methyl-3-trimethylsilanylethynyl-pyridin-2-ylamino)-1H-pyrazin-2-one → 7-Benzyl-3-methyl-5-trimethylsilanyl-7,9-dihydro-dipyrido[2,3-b; 4',3'-d]pyrrol-8-one

HRID 1642513Notes

Reaction equation

[CH2:1]([N:8]1[CH:13]=C(Cl)N=[C:10]([NH:15][C:16]2[C:21]([C:22]#[C:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][C:19]([CH3:28])=[CH:18][N:17]=2)[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>BrC1C=CC=CC=1>[CH2:1]([N:8]1[CH:13]=[C:23]([Si:24]([CH3:26])([CH3:25])[CH3:27])[C:22]2[C:21]3[CH:20]=[C:19]([CH3:28])[CH:18]=[N:17][C:16]=3[NH:15][C:10]=2[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Compound 27 (3.5 g, 8.29 mmol) was dissolved in bromobenzene (150 mL). The solution was heated at 140° C. under N2 and monitored by LC every hour. The reaction was complete after 7 hours. The solution was evaporated and purified by flash chromatography (3% MeOH/CH2Cl2) to give 2.5 g (83%) of intended product as a tan solid. 1H NMR (400 MHz, CDCl3): δ 8.22 (s, 1H), 7.27-7.39 (m, 6H), 5.40 (s, 2H), 2.57 (s, 3H). MS (ES) [m+H] calc'd for C21H23N3OSi, 362; found 362.

Workup

waitmonitored by LC every hour
customThe solution was evaporated
custompurified by flash chromatography (3% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-b29d9c0ab2704619a0ee19f38b868763
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119655B2

Reaction notes

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