Sodium Carbonate → HCID 86761319, compound

HRID 551275Notes

Reaction equation

HRID 551275 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](B(O)O)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH:26]=[C:25](OS(C(F)(F)F)(=O)=O)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[NH4+]>C(#N)C>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH:24]=[C:25]([C:9]2[CH:10]=[C:11]3[C:6]([CH:5]=[CH:4][N:3]=[C:2]3[Cl:1])=[CH:7][CH:8]=2)[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 433294Lithium ChlorideHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 59887844HCID 59887844, compound

Product 1

HCID 86761319HCID 86761319, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Chloroisoquinolin-7-yl boronic acid (0.55 g, 2.67 mmol), 4-(trifluoromethanesulfonyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.68 g, 2.05 mmol), lithium chloride (0.26 g, 6.16 mmol), 2M aqueous sodium carbonate (2.9 ml, 5.8 mmol) and acetonitrile (15 mL) were combined under nitrogen, and palladium tetrakistriphenylphosphine (0.12 g, 0.103 mmol) added. The reaction mixture was refluxed for 90 minutes, cooled to room temperature, and concentrated in vacuo to give a wet solid. Ammonium hydroxide (3 mL of 30% aqueous solution) was added, and the material partitioned between methylene chloride (150 mL) and 2M aqueous sodium carbonate (25 mL). The organic phase was separated, and the aqueous extracted successively with methylene chloride. The combined organic extracts were dried over magnesium sulfate, and purified by flash column chromatography on silica gel to give the product as a white solid (0.43 g, 1.25 mmol). 1H NMR (CDCl3) δ 8.26-8.20 (m, 2H), 7.88-7.75 (m, 2H), 7.57 (d, 1H), 6.28 (br s, 1H), 4.20-4.12 (m, 2H), 3.76-3.66 (m, 2H), 2.75-2.62 (m, 2H), 1.56 (s, 9H). ESI MS (M+1)+: 259, 261 (Cl).

Workup

  1. temperatureThe reaction mixture was refluxed for 90 minutes
  2. concentrationconcentrated in vacuo
  3. customto give a wet solid
  4. customthe material partitioned between methylene chloride (150 mL) and 2M aqueous sodium carbonate (25 mL)
  5. customThe organic phase was separated
  6. extractionthe aqueous extracted successively with methylene chloride
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f86c15abd3a94e248be0cfed91d9a637
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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