Benzyl Bromide → HCID 69591834, compound

HRID 1795963Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[CH:16][N:17]2[C:22]=1[C:21](=[O:23])[NH:20][C:19]([CH3:24])=[N:18]2)=[O:13])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[CH:16][N:17]2[C:22]=1[C:21](=[O:23])[N:20]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:19]([CH3:24])=[N:18]2)=[O:13])[CH3:10]

Participants

Conditions

Temperature: 95 °C

Procedure

Benzyl bromide (0.112 ml, 0.945 mmol) was added to a solution of 2-methyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-5-carboxylic acid ethyl ester (0.19 g, 0.86 mmol) and Cs2CO3 (0.34 g, 1.06 mmol) in dioxane (5 mL) and the reaction mixture was heated to 95° C. for 3 h. The reaction mixture was quenched with saturated NaCl (100 mL), extracted with CHCl3 (3×50 mL), the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 1/1 hexane/EtOAc to afford the title compound as a solid (0.19 g, 70%): 1H NMR (CDCl3) δ 7.22–7.35 (m, 6H), 7.00–7.01 (m, 1H), 5.28 (s, 2H), 4.38 (q, 2H, J=7.19 Hz), 2.38 (s, 3H), 1.38 (t, 3H, J=7.09 Hz); MS (ESI+) 312 (M++H).

Workup

customThe reaction mixture was quenched with saturated NaCl (100 mL)
extractionextracted with CHCl3 (3×50 mL)
dry with materialthe combined organic extracts dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel eluting with 1/1 hexane/EtOAc

Sources & evidence

ORD record: ord-1651edd2df254c308ec17f77f14aa6f6
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030118B2

Reaction notes

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