Dichloromethane → HCID 86607409, compound

HRID 29249

Reaction equation

HRID 29249 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[O:12][C:13]2[CH:20]=[C:19](B3OC(C)(C)C(C)(C)O3)[CH:18]=[CH:17][C:14]=2[C:15]=1[CH3:16])=O.Br[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([NH2:36])=[O:35].ClCCl.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:11]1[O:12][C:13]2[CH:20]=[C:19]([C:32]3[CH:31]=[CH:39][CH:38]=[CH:37][C:33]=3[C:34]([NH2:36])=[O:35])[CH:18]=[CH:17][C:14]=2[C:15]=1[CH3:16]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 898073-BromobenzamideHCID 59788883HCID 59788883, compound

Product 1

HCID 86607409HCID 86607409, compoundYield 43.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of (2,4-dichlorophenyl)-[3-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-benzofuran-2-yl]-methanone (100 mg, 0.23 mmol) in toluene (4 mL) and ethanol (4 mL) was added 3-bromobenzamide (56 mg, 0.28 mmol) followed by [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium (II), complex with dichloromethane (1:1) (17 mg, 0.02 mmol) and 2M aqueous Na2CO3 (0.29 mL, 0.58 mmol). The mixture was degassed under vacuum, then heated to 85 C for 2 h. The reaction mixture was concentrated in vacuo, diluted in methanol, and filtered through a syringe filter. Purification by prep-HPLC provided the desired material as a white solid (41.3 mg, 42%). 1H-NMR (CDCl3) δ 8.02 (t, J=1.9 Hz, 1H), 7.71-7.67 (m, 3H), 7.61 (m, 1H), 7.52 (dd, J=1.4, 8.4 Hz, 1H), 7.46 (t, J=7.7 Hz, 1H), 7.43 (d, J=2.0 Hz, 1H), 7.39 (m, 1H), 7.31 (ddd, J=8.1, 1.9, 0.2 Hz, 1H), 2.54 (s, 3H).

Workup

  1. customThe mixture was degassed under vacuum
  2. temperatureheated to 85 C for 2 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted in methanol
  5. filtrationfiltered through a syringe
  6. filtrationfilter
  7. customPurification

Sources & evidence

ORD record
ord-fa709c035eeb4258bf3f4196f56c05f8
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Linked notes

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