Ethanol → HCID 68455222, compound

HRID 2357627Notes

Reaction equation

HRID 2357627 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:7]=2)[CH2:3][CH2:2]1.Br[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30]([N:34]1[CH:38]([CH3:39])[CH2:37][CH2:36][C@@H:35]1[C:40]([NH:42][CH:43]([CH3:45])[CH3:44])=[O:41])=[N:29][N:28]=[CH:27]2.C(O)C.C(=O)([O-])[O-].[K+].[K+].O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([NH:4][C:5]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[C:30]([N:34]3[CH:38]([CH3:39])[CH2:37][CH2:36][C@@H:35]3[C:40]([NH:42][CH:43]([CH3:45])[CH3:44])=[O:41])=[N:29][N:28]=[CH:27]4)[CH:7]=2)=[O:22])[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 702EthanolHCID 962WaterHCID 11430Potassium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 68454221HCID 68454221, compound

Product 1

HCID 68455222HCID 68455222, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-Cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (64 mg, 212 μmol), tetrakis(triphenylphosphine)palladium (18 mg, 16 μmol), and (R)-1-(6-bromophthalazin-1-yl)-N-isopropyl-5-methylpyrrolidine-2-carboxamide (40 mg, 106 μmol) were dissolved/suspended in ethanol (2120 μl, 106 μmol) before potassium carbonate −1 M in water (424 μl, 424 μmol) was added to the vial which was then placed in the microwave for 10 min at 160° C. The reaction mixture was diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give crude. After purification by chromatography, the title compound was obtained. MS (ES+): 472 (M+H)+.

Workup

  1. additionwas added to the vial which
  2. additionadded to a separation funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washwashed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give crude
  9. customAfter purification by chromatography

Sources & evidence

ORD record
ord-d4dc66ffb954401893f8d14cccb69d00
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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