Potassium Carbonate → HCID 54767213, compound

HRID 336119Notes

Reaction equation

HRID 336119 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([B:23]2[O:31][C:28]([CH3:30])([CH3:29])[C:25]([CH3:27])([CH3:26])[O:24]2)=[CH:19][CH:18]=1>CN(C=O)C>[CH3:29][C:28]1([CH3:30])[C:25]([CH3:26])([CH3:27])[O:24][B:23]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][O:8][N:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]3=[O:1])=[CH:22][CH:21]=2)[O:31]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178526252HCID 178526252, compound

Product 1

HCID 54767213HCID 54767213, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-hydroxypyridine-1-oxide (0.04 g, 0.34 mmol) was dissolved in 5 mL of anhydrous DMF. To this was added K2CO3 (0.14 g, 1.02 mmol) and 4-bromomethylphenyl boronic acid pinacol ester (0.10 g, 0.34 mmol). The reaction was heated to 80° C. and allowed to stir under nitrogen overnight. After cooling to room temperature, the solvent was evaporated and the resulting residue was brought up in dichloromethane and washed twice with water. The organic layer was dried over MgSO4, filtered and concentrated for purification via silica gel chromatography eluting with 2% MeOH in DCM. The protected B19 was collected as an off-white solid in 87% yield (98 mg, 0.3 mmol). 1H NMR (400 MHz, CDCl3) δ=7.79 (d, J=8.0 Hz, 2H), 7.38 (d, J=8.0 Hz, 2H), 7.24 (td, J=7.2 Hz, J2=2.0 Hz, 1H), 7.05 (dd, J=7.2 Hz, J2=2.0 Hz, 1H), 6.67 (dd, J=9.2 Hz, J2=1.2 Hz, 1H), 5.89 (td, J=6.8 Hz, J2=1.6 Hz, 1H), 5.29 (s, 2H), 1.35 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=159.2, 138.9, 137.0, 136.8, 135.3, 129.5, 122.9, 104.7, 84.3, 78.4, 25.1. ESI-MS(+): m/z 328.18 [M+H]+. Anal. calcd. for C18H22BNO4. 0.4 CH3OH: C, 65.26; H, 6.94; N, 4.16. Found: C, 65.54; H, 7.20; N, 3.76.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated
  3. washwashed twice with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated for purification via silica gel chromatography
  7. washeluting with 2% MeOH in DCM
  8. customThe protected B19 was collected as an off-white solid in 87% yield (98 mg, 0.3 mmol)

Sources & evidence

ORD record
ord-47c46ce9d1484f52b92310e0dec63b2d
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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