Sodium Carbonate → HCID 86676191, compound

HRID 594184Notes

Reaction equation

HRID 594184 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH2:22][C@@H:23]3[N:29]([CH:30]=2)[C:28](=[O:31])[C:27]2[CH:32]=[C:33]([O:74][CH3:75])[C:34]([O:36][CH2:37][CH2:38][CH2:39][O:40][C:41]4[C:71]([O:72][CH3:73])=[CH:70][C:44]5[C:45](=[O:69])[N:46]6[CH:61]=[C:60](S(C(F)(F)F)(=O)=O)[CH2:59][C@H:47]6[C:48](=[O:58])[N:49]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[C:43]=5[CH:42]=4)=[CH:35][C:26]=2[N:25]([CH2:76][O:77][CH2:78][CH2:79][Si:80]([CH3:83])([CH3:82])[CH3:81])[C:24]3=[O:84])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:60]2[CH2:59][C@@H:47]3[N:46]([CH:61]=2)[C:45](=[O:69])[C:44]2[CH:70]=[C:71]([O:72][CH3:73])[C:41]([O:40][CH2:39][CH2:38][CH2:37][O:36][C:34]4[C:33]([O:74][CH3:75])=[CH:32][C:27]5[C:28](=[O:31])[N:29]6[CH:30]=[C:21]([C:18]7[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=7)[CH2:22][C@H:23]6[C:24](=[O:84])[N:25]([CH2:76][O:77][CH2:78][CH2:79][Si:80]([CH3:81])([CH3:83])[CH3:82])[C:26]=5[CH:35]=4)=[CH:42][C:43]=2[N:49]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:55])([CH3:56])[CH3:57])[C:48]3=[O:58])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343114-Aminomethylphenylboronic acid hydrochlorideHCID 86676188HCID 86676188, compound

Product 1

HCID 86676191HCID 86676191, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

Solid 4-aminomethylbenzeneboronic acid hydrochloride (0.111 g, 0.59 mmol) was added to a solution of 17 (0.394 g, 0.37 mmol), sodium carbonate (175 mg, 1.654 mmol) and palladium tetrakis triphenylphosphine (28.0 mg, 0.024 mmol) in toluene (10 mL), ethanol (5 mL) and water (5 mL). The reaction mixture was allowed to stir overnight at 30° C. The following day the reaction mixture was heated for a further 3 hours at 70° C. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulphate. Excess solvent was removed by rotary evaporation under reduced pressure and the resulting residue was subjected to flash column chromatography (silica gel; gradient elution EtOAc/hexane 2/98→15/85). Removal of excess eluent from selected fractions afforded the desired product (0.230 mg, 0.22 mmol, 61%).

Workup

  1. temperatureThe following day the reaction mixture was heated for a further 3 hours at 70° C
  2. customThe reaction mixture was then partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customExcess solvent was removed by rotary evaporation under reduced pressure
  6. washthe resulting residue was subjected to flash column chromatography (silica gel; gradient elution EtOAc/hexane 2/98→15/85)
  7. customRemoval of excess eluent

Sources & evidence

ORD record
ord-1817dcfc6de1414da79c9388ccb5740c
Source dataset
uspto-grants-2016_01
Patent number
US09242013B2

Reaction notes

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