Potassium Carbonate → HCID 86640965, compound

HRID 906411Notes

Reaction equation

HRID 906411 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:17]=[C:16]([CH:18]=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[C:9]1=[O:21])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH:28]1([NH:31][C:32](=[O:50])[C:33]2[CH:38]=[C:37](B3OC(C)(C)C(C)(C)O3)[C:36]([CH3:48])=[C:35]([F:49])[CH:34]=2)[CH2:30][CH2:29]1>CN(C=O)C.O>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:17]=[C:16]([CH:18]=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:37]3[CH:38]=[C:33]([C:32](=[O:50])[NH:31][CH:28]4[CH2:29][CH2:30]4)[CH:34]=[C:35]([F:49])[C:36]=3[CH3:48])[CH:14]=2)[C:9]1=[O:21])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21914563N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 57439897HCID 57439897, compound

Product 1

HCID 86640965HCID 86640965, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(6-Bromo-4-formyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (Example 10c, 0.90 g), potassium carbonate (1.06 g), N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.82 g) and Pd-118 (0.050 g) in DMF (10 ml) were heated under nitrogen at 70° C. for 12 h. The cooled reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and evaporated. The residue was purified (SiO2 chromatography, elution with ethyl acetate) to afford the subtitle compound.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified
  7. wash(SiO2 chromatography, elution with ethyl acetate)

Sources & evidence

ORD record
ord-b3455a2d095f4fff81c13d28320d4cef
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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