Potassium Carbonate → HCID 57816838, compound

HRID 2197479Notes

Reaction equation

HRID 2197479 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][NH:12]2)=[C:8]([NH2:15])[N:7]=1)[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)[CH2:27][P:28]([CH3:33])(=[O:32])[O:29][CH2:30][CH3:31]>CN(C=O)C>[NH2:15][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[CH2:23][C:24]1[CH:25]=[C:26]([CH2:27][P:28]([CH3:33])(=[O:32])[O:29][CH2:30][CH3:31])[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57816773Ethyl 3-(bromomethyl)benzyl(methyl)phosphinateHCID 178450368HCID 178450368, compound

Product 1

HCID 57816838HCID 57816838, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 59 (300.0 mg, 1.45 mmol) and K2CO3 (200.0 mg, 1.45 mmol) was dissolved in DMF (5 mL) and to it was added 65 (421.0 mg, 1.45 mmol). The mixture was left to stir over night at room temperature, solvent was evaporated by rotary evaporation. The remaining solid was taken up in water and the product extracted with DCM (3×50 mL). Combined organic layers were washed with water (1×50 mL) and brine (2×50 mL) and dried over Na2SO4. Product was purified by flash column eluting 0-10% methanol in ethyl acetate to give 204.0 mg (34%) 68 as a solid. 1H NMR (300 MHz, CDCl3) δ 0.923 (t, 3H), 1.19 (t, 3H), 1.31 (d, 3H), 1.44 (m, 2H), 1.73 (m, 2H), 3.07 (dd, 2H), 3.94 (m, 2H), 4.28 (t, 2H), 5.24 (s, 2H), 7.17 (m, 4H), 7.59 (s, 1H). LCMS: m/z for C20H28N5O3P++H observed 418.2 at 2.03 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O.

Workup

  1. waitThe mixture was left
  2. customsolvent was evaporated by rotary evaporation
  3. extractionthe product extracted with DCM (3×50 mL)
  4. washCombined organic layers were washed with water (1×50 mL) and brine (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. customProduct was purified by flash column
  7. washeluting 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-a1b61e88a70c47f2ba7d3db430ad7199
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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