Methyl iodide → Ethyl 2-(4-chloro-1-hydroxy-6-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798097Notes

Reaction equation

HRID 1798097 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([OH:18])[CH:3]=1.IC.[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58292598Ethyl 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292815Ethyl 2-(4-chloro-1-hydroxy-6-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetateYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (150 mg, 0.55 mmol) and iodomethane (254 mg, 2.22 mL) in anhydrous DMF (2 mL) was added anhydrous K2CO3 (380 mg, 2.75 mmol). The reaction mixture was stirred for 10 h and concentrated under reduced pressure. The residue was purified by prep HPLC to give the title compound as a yellow oil (49.1 mg. Yield: 31%). 1H NMR (400 MHz, DMSO-d6) δ 9.45 (s, 1H), 7.22-7.23 (d, J=4.0 Hz, 1H), 7.14-7.15 (d, J=4.0 Hz, 1H), 5.45-5.48 (m, 1H), 4.03-4.09 (m, 2H), 3.81 (s, 3H), 3.21-3.25 (m, 1H), 2.39-2.45 (m, 1H), 1.14-1.17 (m, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-71467cd54a80453a916aea28500c3cdd
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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