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Dichloromethane → 1-methyl-2-(2'-nitrobiphenyl-4-yl)-1H-benzo[d]imidazole

HRID 1509643
Notes
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Reaction equation

HRID 1509643 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[CH3:17][N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>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]>[CH3:17][N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 958901H-Benzimidazole, 1-methyl-HCID 6297494'-Iodo-2-nitrobiphenyl

Product 1

HCID 1181139891-methyl-2-(2'-nitrobiphenyl-4-yl)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst

Conditions

Temperature
65 °C

Procedure

To a three-necked flask equipped with a magnetic stir bar was added 4′-iodo-2-nitrobiphenyl (3.90 g, 12.0 mmol, 1.2 equiv), 1-methyl-1H-benzo[d]imidazole (1.32 g, 10.0 mmol, 1.0 equiv), Ag2CO3 (5.52 g, 20.0 mmol, 2.0 eq), Pd(dppf)Cl2.CH2Cl2 (0.41 g, 0.5 mmol, 0.05 eq) and PPh3 (0.26 g, 1.0 mmol, 0.1 eq). The tube was evacuated and back-filled with nitrogen, and this evacuation/back-fill procedure was repeated twice. Then solvent CH3CN (60 mL) was added under the protection of nitrogen. The mixture was stirred in an oil bath at a temperature of 60-70° C. for 6.5 days and then cooled. The solid was filtered off through a pad of celite, and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (10:1-5:1-3:1-2:1) as an eluent to afford the desired product, 1-methyl-2-(2′-nitrobiphenyl-4-yl)-1H-benzo[d]imidazole, as a white solid (1.36 g in 41% yield). 1H NMR (DMSO-d6, 400 MHz): δ 3.95 (s, 3H), 7.25-7.29 (m, 1H), 7.31-7035 (m, 1H), 7.57 (d, J=8.0 Hz, 2H), 7.65-7.72 (m, 4H), 7.84 (td, J=7.6, 1.2 Hz, 1H), 7.98 (d, J=7.6 Hz, 2H), 8.06-8.08 (m, 1H).

Workup

  1. customTo a three-necked flask equipped with a magnetic stir bar
  2. customThe tube was evacuated
  3. additionback-filled with nitrogen
  4. additionThen solvent CH3CN (60 mL) was added under the protection of nitrogen
  5. temperaturecooled
  6. filtrationThe solid was filtered off through a pad of celite
  7. washwashed with ethyl acetate
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified through column chromatography on silica gel

Sources & evidence

ORD record
ord-9f5a1f07d8bd44ffba91080577dbbf36
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09224963B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes