Potassium Carbonate → HCID 68453824, compound

HRID 2357671Notes

Reaction equation

HRID 2357671 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)#[N:26].C(=O)([O-])[O-:37].[K+].[K+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:26][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1)=[O:37]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27346102-Cyanophenylboronic acidHCID 118483123-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 68453824HCID 68453824, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

The title compound was prepared by a method analogous to that described in Example 11 (Method D), using a mixture of 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (0.111 g, 0.33 mmol), 2-cyanophenylboronic acid (0.211 g, 1.4 mmol), potassium carbonate (0.400 g, 2.9 mmol) and trans-dichlorobis(triphenyl-phosphine)palladium (II) (0.017 g, 0.024 mmol) in 1.4 mL DME/0.6 mL H2O/0.4 mL EtOH, which was heated at 120° C. for 15 min. The mixture was partitioned between ethyl acetate/brine and the aqueous layer was extracted with ethyl acetate (3×). The combined organics were evaporated onto silica gel and purified using flash chromatography eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→7:93) to afford the title compound as an amorphous white solid. Found MS m/z: 423 [M+1].

Workup

  1. customThe title compound was prepared by a method analogous to
  2. customThe mixture was partitioned between ethyl acetate/brine
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  4. customThe combined organics were evaporated onto silica gel
  5. custompurified
  6. washeluting with 2M NH3 in MeOH:CH2Cl2 (0:1→7:93)

Sources & evidence

ORD record
ord-1ac61360ef134716b3b18fb7c6c28540
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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