1,4-Dioxane → (1-{4-[3-(2-Methoxy-phenyl)-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl]-phenyl}-cyclobutyl)-carbamic Acid Tert-butyl Ester

HRID 2362161Notes

Reaction equation

HRID 2362161 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[C:30](Br)=[CH:31][N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[O:44]1CCOC[CH2:45]1>C(Cl)Cl.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[C:30]([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=5[O:44][CH3:45])=[CH:31][N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 66665726{1-[4-(3-Bromo-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

Product 1

HCID 66719135(1-{4-[3-(2-Methoxy-phenyl)-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl]-phenyl}-cyclobutyl)-carbamic Acid Tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound 4-3 (52 mg 0.1 mmol), 2-methoxy]phenyl boronic acid (30 mg, 0.15 mmol), aq.Na2 CO3 (2M, 0.25 mmol, 0.12 mL) and Pd(DPPF)Cl2 (10 mg) in dioxane (3 mL) was heated at 100° C. in microwave system under N2 atmosphere for 30 min. After cooling, the mixture was diluted with 15 mL of DCM, the combined organic phase was washed with 0.1N HCl aq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 36 mg of 4-7.

Workup

  1. temperatureAfter cooling
  2. washthe combined organic phase was washed with 0.1N HCl aq and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep.TLC

Sources & evidence

ORD record
ord-e7ec0f5791d64a9c8d8c2cc4c639d3cc
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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