Benzyl Bromide → HCID 22180078, compound

HRID 1795953Notes

Reaction equation

HRID 1795953 reaction equation
[Cl:1][C:2]1[N:10]2[C:5]([C:6](=[O:12])[NH:7][C:8]([CH3:11])=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1.O>[CH2:19]([N:7]1[C:6](=[O:12])[C:5]2=[CH:4][CH:3]=[C:2]([Cl:1])[N:10]2[N:9]=[C:8]1[CH3:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 135752502HCID 135752502, compound

Product 1

HCID 22180078HCID 22180078, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred mixture of 7-chloro-2-methyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (1.10 g, 5.99 mmol) and Cs2CO3 (2.25 g, 6.9 mmol) in dioxane (20 mL) was added benzyl bromide (0.76 mL, 6.16 mmol) and heated at 95° C. under nitrogen for 3 h. The reaction mixture was cooled to rt, diluted with water and stirred for 1 h. The precipitated solid was collected and washed with water, dried in vaccum over P2O5 at 35° C. to give the title compound (1.41 g, 87%): 1H NMR (CDCl3) δ 7.26 (m, 2H), 7.20 (m, 1H), 7.13 (m, 2H), 6.98 (d, 1H, J=4.4 Hz), 6.40 (d, 1H, J=4.4 Hz), 5.19 (s, 2H), 2.35 (s, 3H); 3C NMR (CDCl3) δ 154.0, 148.0, 135.8, 129.0, 127.8, 126.5, 117.7, 116.5, 109.7, 108.2, 45.7, 20.1; MS (ESI+) 274.04, 276.06 (M++H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customThe precipitated solid was collected
  3. washwashed with water
  4. dry with materialdried in vaccum over P2O5 at 35° C.

Sources & evidence

ORD record
ord-0cb3cfa918c143e8ad30fb6418a3b43b
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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