Dichloromethane → 5-benzyl-5-(4-pyridin-3-ylphenyl)-5H-imidazo[2,1-a]isoindole

HRID 46165Notes

Reaction equation

HRID 46165 reaction equation
[CH2:1]([C:8]1([C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2=[N:17][CH:18]=[CH:19][N:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.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].C1COCC1>[CH2:1]([C:8]1([C:20]2[CH:25]=[CH:24][C:23]([C:29]3[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=3)=[CH:22][CH:21]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2=[N:17][CH:18]=[CH:19][N:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 462065995-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole

Product 1

HCID 462062545-benzyl-5-(4-pyridin-3-ylphenyl)-5H-imidazo[2,1-a]isoindole

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 5-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole (30 mg), 3-pyridylboronic acid (18 mg) and [PdCl2(dppf)].CH2Cl2 (6 mg) was added THF (2 mL) followed by aqueous Na2CO3 (0.112 mL, 2 M). The reaction vessel was then sealed and heated at 150° C. under microwave irradiation for 20 minutes. The reaction mixture was then diluted with EtOAc and the organic layer was collected and concentrated. Purification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-40% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min) afforded the title compound as a white solid. HRMS. Found, 400.1805; calcd for (M+H)+, 400.1808. 1H NMR (500 MHz, CDCl3): δ 8.84 (d, J=1.9 Hz, 1H), 8.61 (dd, J=4.9, 1.5 Hz, 1 H), 7.86-7.84 (m, 1 H), 7.65-7.58 (m, 3H), 7.45-7.26 (m, 7H), 7.05-7.03 (m, 1H), 6.99-6.95 (m, 3H), 6.60 (d, J=7.3 Hz, 2H), 3.89-3.83 (m, 2H).

Workup

  1. customThe reaction vessel was then sealed
  2. customthe organic layer was collected
  3. concentrationconcentrated
  4. customPurification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-40% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min)

Sources & evidence

ORD record
ord-9657fe770ddc49d8a0f7e1c7c12b47d0
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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