Potassium Carbonate → HCID 67391407, compound

HRID 906443Notes

Reaction equation

HRID 906443 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][C:14]([CH3:25])([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:6]=[C:5]2[S:26]([N:29]1[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31][CH2:30]1)(=[O:28])=[O:27].[CH:43]1([NH:46][C:47](=[O:65])[C:48]2[CH:53]=[C:52](B3OC(C)(C)C(C)(C)O3)[C:51]([CH3:63])=[C:50]([F:64])[CH:49]=2)[CH2:45][CH2:44]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Si:17]([O:16][CH2:15][C:14]([CH3:24])([CH3:25])[CH2:13][N:7]1[CH:6]=[C:5]([S:26]([N:29]2[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31][CH2:30]2)(=[O:28])=[O:27])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:52]3[CH:53]=[C:48]([C:47](=[O:65])[NH:46][CH:43]4[CH2:44][CH2:45]4)[CH:49]=[C:50]([F:64])[C:51]=3[CH3:63])[CH:3]=2)[C:8]1=[O:12])([C:20]([CH3:21])([CH3:23])[CH3:22])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21914563N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 67389644HCID 67389644, compound

Product 1

HCID 67391407HCID 67391407, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of tert-butyl 4-{[6-bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-4-yl]sulfonyl}-1,4-diazepane-1-carboxylate (Example 46c, 83 mg) in DMF (2 mL) was treated with N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (39 mg), Pd-118 (2.4 mg) and potassium carbonate (33 mg) under nitrogen. The resulting mixture was stirred at 70° C. for 1 h. The cooled reaction mixture was partitioned between ethyl acetate and water. The aqueous was extracted with ethyl acetate (2×100 mL). The combined organics were washed with water (3×100 mL), brine (3×100 mL) dried (MgSO4), filtered, and evaporated under reduced pressure. The crude product was purified (SiO2 chromatography, elution with 50% ethyl acetate/isohexane) to afford the subtitle compound (0.055 g).

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. extractionThe aqueous was extracted with ethyl acetate (2×100 mL)
  4. washThe combined organics were washed with water (3×100 mL), brine (3×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product was purified
  9. wash(SiO2 chromatography, elution with 50% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-c52b6d1acf884c38a93efa610d99b3f6
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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