Water → HCID 66727313, compound

HRID 1845961Notes

Reaction equation

HRID 1845961 reaction equation
Br[C:2]1[C:11]([S:12]([N:15]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][C@@H:16]2[CH3:29])(=[O:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[CH3:30]B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([O:24][C:22]([N:18]1[CH2:19][CH2:20][CH2:21][N:15]([S:12]([C:11]2[C:2]([CH3:30])=[C:3]3[C:8](=[CH:9][CH:10]=2)[CH:7]=[N:6][CH:5]=[CH:4]3)(=[O:14])=[O:13])[C@@H:16]([CH3:29])[CH2:17]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 66726691HCID 66726691, compound

Product 1

HCID 66727313HCID 66727313, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

100 mg of (S)-5-bromo-6-(4-tert-butoxycarbonyl-2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline, 15 mg of methylboronic acid, 12 mg of tetrakis(triphenylphosphine)palladium, and 131 mg of potassium phosphate were suspended in 10 mL of 1,4-dioxane and stirred at 100° C. for 10 hours in an argon gas atmosphere. After the completion of reaction, water was added to the reaction solution, followed by extraction with ethyl acetate (30 mL×2). Then, the extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 70 mg of the compound of interest as a colorless oil (81%).

Workup

  1. additionwas added to the reaction solution
  2. extractionfollowed by extraction with ethyl acetate (30 mL×2)
  3. dry with materialThen, the extract was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-2158d867929f48f79513b32ab1dc33e3
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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