Sarcosine → 2-Bromo-6-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-trien-5-yl}benzaldehyde

HRID 519399Notes

Reaction equation

[C:1]12[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=1[S:8][C:7]1[C:6](=[O:14])[NH:5][N:4]=[CH:3][C:2]2=1.[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[C:17]=1[CH:18]=[O:19].N(CC(O)=O)C.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([N:5]2[C:6](=[O:14])[C:7]3[S:8][C:9]4[CH2:10][CH2:11][CH2:12][CH2:13][C:1]=4[C:2]=3[CH:3]=[N:4]2)[C:17]=1[CH:18]=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (20 mL), 8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-trien-6-one 117c (618 mg, 3.0 mmol), 2,6-dibromobenzaldehyde (1980 mg, 7.5 mmol), CuBr (215 mg, 1.5 mmol), sarcosine (267 mg, 3.0 mmol), and K2CO3 (828 mg, 6.0 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 16 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 130a (702 mg, 60%) as a yellow solid. MS: [M+H]+ 389.0

Workup

customA 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
customAfter three cycles of vacuum/argon flush
temperatureAfter this time the reaction was cooled to room temperature
filtrationIt was then filtered
customthe filtrate was evaporated under reduced pressure
customThe residue was purified by silica-gel column chromatography
washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record: ord-d6c6500de8a541c6a23147b9011ad863
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115152B2

Reaction notes

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