Potassium Carbonate → HCID 67390832, compound

HRID 906446Notes

Reaction equation

HRID 906446 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[CH:6]=[C:5]2[S:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)(=[O:19])=[O:18].[CH:33]1([NH:36][C:37](=[O:55])[C:38]2[CH:43]=[C:42](B3OC(C)(C)C(C)(C)O3)[C:41]([CH3:53])=[C:40]([F:54])[CH:39]=2)[CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH:33]1([NH:36][C:37]([C:38]2[CH:39]=[C:40]([F:54])[C:41]([CH3:53])=[C:42]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8](=[O:12])[N:7]([CH2:13][CH:14]3[CH2:15][CH2:16]3)[CH:6]=[C:5]4[S:17]([N:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:24][CH2:25]3)(=[O:19])=[O:18])[CH:43]=2)=[O:55])[CH2:35][CH2:34]1

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 67130358HCID 67130358, compound

Product 1

HCID 67390832HCID 67390832, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of tert-butyl 4-{[6-bromo-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinolin-4-yl]sulfonyl}piperazine-1-carboxylate (Example 47b, 0.890 g) in DMF (10 mL) was treated with N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide (0.491 g), Pd-118 (0.030 g) and potassium carbonate (0.425 g). The mixture was stirred at 70° C. for 1 h. The cooled reaction mixture was diluted with water (100 mL), and extracted into ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (3×100 mL), dried (MgSO4), filtered and evaporated. The crude product was purified (SiO2 chromatography, elution with 10% ethyl acetate/DCM) to afford the subtitle compound (0.713 g) as beige foam, which was used without further analysis.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted into ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with brine (3×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified
  8. wash(SiO2 chromatography, elution with 10% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-2b0fceea17c9410d882e37f83244e110
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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