Benzyl Bromide → HCID 59226034, compound

HRID 38446Notes

Reaction equation

HRID 38446 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[NH:7][CH:6]=[CH:5]2.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1.C(OCC)(=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:14]([O:13][C:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([CH3:12])[CH:10]=2)[CH:5]=[CH:6][N:7]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 7498Benzyl Bromide2×HCID 592260506-Fluoro-7-methylisoquinolin-1(2H)-one

Product 1

HCID 59226034HCID 59226034, compoundYield 15.1%

Reagents, catalysts & solvents 3

HCID 178418647HCID 178418647, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

6-Fluoro-7-methyl-2H-isoquinolin-1-one (prepared as described in WO2007012421, 13.2 g, mmol) was dissolved in tetrahydrofurane (175 mL). After addition of silver carbonate (41.2 g), benzyl bromide (15.3 g) was added dropwise. The mixture was stirred overnight. The mixture was heated to 70° C. and another 3 mL of benzyl bromide were added. Heating was continued until no further conversion was observed. The mixture was taken up in ethyl acetate, filtered over celite, evaporated and the residue was taken up in little ethyl acetate. The formed precipitate was filtered off to give 3.0 g of (2). The mother liquor was concentrated and chromatographed on silica gel to yield another 8.6 g of (2). Rt=4.00 min (Method 2). Detected mass: 268.1 (M+H+).

Workup

  1. additionwas added dropwise
  2. temperatureHeating
  3. filtrationfiltered over celite
  4. customevaporated
  5. filtrationThe formed precipitate was filtered off

Sources & evidence

ORD record
ord-87f707211df34d2d8cfc817ce3ac0921
Source dataset
uspto-grants-2013_09
Patent number
US08524737B2

Reaction notes

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