Dichloromethane → HCID 59681752, compound

HRID 1394198Notes

Reaction equation

HRID 1394198 reaction equation
Br[C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:9]([C:17]3[C:18]([NH2:22])=[N:19][O:20][N:21]=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>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]>[C:11]1([N:10]2[C:3]3[C:2]([C:24]4[S:23][CH:27]=[CH:26][CH:25]=4)=[CH:7][N:6]=[CH:5][C:4]=3[N:8]=[C:9]2[C:17]2[C:18]([NH2:22])=[N:19][O:20][N:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27339602-Thiopheneboronic acidHCID 59681831HCID 59681831, compound

Product 1

HCID 59681752HCID 59681752, compoundYield 18%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

A stirred mixture of the product from Example 180 (50 mg, 0.14 mmol), thiophene-2-boronic acid (27 mg, 0.21 mmol) and Pd(dppf)2Cl2.CH2Cl2 (11 mg, 0.014 mmol) in 3.5 ml of 2.5:1 Dioxane/2 M K2CO3 contained in a 20 ml pressure tube was heated to 110° C. for 18 h. The resulting biphase mixture was cooled to room temperature. The organic layer (top) was removed with pipet, filtered to remove the Pd. The aqueous layer was extracted once with EtOAc. EtOAc was combined with the organic filtrate, washed with sat'd NaHCO3, water, brine, dried (Na2SO4) and reduced in vacuo. the residue was purified by silica gel chromatography eluting with 10% MeOH in CHCl3, to afford the title compound, (9 mg, 18%); MS (ES+) m/e 361 [M+H]+.

Workup

  1. temperatureThe resulting biphase mixture was cooled to room temperature
  2. customThe organic layer (top) was removed with pipet
  3. filtrationfiltered
  4. customto remove the Pd
  5. extractionThe aqueous layer was extracted once with EtOAc
  6. washwashed with sat'd NaHCO3, water, brine
  7. dry with materialdried (Na2SO4)
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-f486e1564109445489f258a70da93289
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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