Dichloromethane → HCID 57755920, compound

HRID 227724Notes

Reaction equation

HRID 227724 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([NH:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][N:21]=[CH:20]4)=[O:15])=[C:12]([CH3:26])[NH:11][C:10](=[O:27])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:16][C:17]1[CH:25]=[C:24]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]3[C:13]([C:14]([NH:16][C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[NH:22][N:21]=[CH:20]5)=[O:15])=[C:12]([CH3:26])[NH:11][C:10](=[O:27])[NH:9]3)[CH:3]=2)[CH:23]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 11350801HCID 11350801, compound

Product 1

HCID 57755920HCID 57755920, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
185 °C

Procedure

The product of Example 76 (0.100 g, 0.230 mmol, 1.00 equiv), Pd(dppf)Cl2.CH2Cl2, and 3-aminoboronic acid (107 mg, 0.690 mmol, 3.00 equiv) were dissolved in dioxane (2 mL) and 1M aq. Na2CO3 (0.690 mL, 0.690 mmol, 3.00 equiv) was added. The reaction mixture was heated to 185° C. In a SmithSynthesizer for 6 minutes. The crude reaction mixture was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (30×100 Xterra prep, 25-80% CH3CN/5 mM NH4HCO3 over 18 minutes) to afford the title compound as a white solid. MS (ES+) m/e 439 [M+H]

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by reverse phase HPLC (30×100 Xterra prep, 25-80% CH3CN/5 mM NH4HCO3 over 18 minutes)

Sources & evidence

ORD record
ord-06de7c2424274d7fae6b5c6083898881
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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