Cesium carbonate → HCID 68693234, compound

HRID 2236936Notes

Reaction equation

HRID 2236936 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[CH:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:7](=[O:12])[NH:8][CH2:9]2)=[CH:4][CH:3]=1.C(OC([N:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(O)O)=O)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][CH:13]=[C:6]2[C:5]3[C:10](=[CH:11][C:2]([C:31]4[NH:30][CH:34]=[CH:33][CH:32]=4)=[CH:3][CH:4]=3)[CH2:9][NH:8][C:7]2=[O:12])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 68692783HCID 68692783, compound

Product 1

HCID 68693234HCID 68693234, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

To a suspension of 7-bromo-4-[(4-methoxy-phenylamino)-methylene]-1,4-dihydro-2H-isoquinolin-3-one (36 mg, 0.1 mmol) in N,N-dimethylformamide (1 mL) is add 1-(t-butoxycarbonyl)pyrrole-2-boronic acid (25.3 mg, 0.12 mmol), 2 M aqueous solution of cesium carbonate (300 μL) and tetrakis(triphenylphosphine)-palladium (0) (30 mg). The reaction mixture is heated in a microwave at 180° C. for 5 min. The reaction mixture is then filtered and the filtrate is purified by Prep. HPLC. The pure fractions were combined and concentrated to yield the title compound (12.8 mg).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customthe filtrate is purified by Prep
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9666584f8d394be1a1d0b0155204c655
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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