Ethanol → HCID 10112602, compound

HRID 1297084Notes

Reaction equation

HRID 1297084 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[CH2:12][C:11](=[O:23])[N:10]([CH3:24])[N:9]=2)=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CCO>C1(C)C=CC=CC=1.O>[CH3:20][O:19][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:14]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][CH3:25])=[CH:3][CH:4]=3)=[N:9][N:10]([CH3:24])[C:11](=[O:23])[CH2:12][C:13]=2[CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 10160160HCID 10160160, compound

Product 1

HCID 10112602HCID 10112602, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Heat at 90° C. for 12 hours under an inert atmosphere a mixture of 100 mg (0.229 mmol) of 1-(4-iodophenyl)-7,8-dimethoxy-3-methyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one IIIah, 38 mg (0.25 mmol) of 2-methoxybenzene boronic acid, 215 μl of 2M Na2CO3, 25 mg (0.020 mmol) of tetrakis(triphenylphosphine)Pd(0) and 250 μl of EtOH in 5 ml of degassed toluene. Allow to cool to room temperature. Add 80 ml of H2O and extract three times with 50 ml of Et2O. Dry the organic fractions on Na2SO4. Purify by chromatography (AcOEt). Recrystallize in Et2O/pentane. The reaction yields 70 mg of the abovenamed product in the form of colorless crystals. Yield: 73%. M: 185–186° C. 1H-NMR (CDCl3, 300 MHz): d 3.40–3.51 (m, 5H, CH2+CH3), 3.78 (s, 3H, CH3), 3.85 (s, 3H, CH3), 3.98 (s, 3H, CH3), 6.80 (s, 1H Ar), 6.89 (s, 1H Ar), 7.04–7.73 (m, 8H Ar).

Workup

  1. temperatureto cool to room temperature
  2. extractionextract three times with 50 ml of Et2O
  3. customDry the organic fractions on Na2SO4
  4. customPurify by chromatography (AcOEt)
  5. customRecrystallize in Et2O/pentane

Sources & evidence

ORD record
ord-f99f00adcfbb42a6b318e010d131df49
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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