Potassium Carbonate → HCID 135526516, compound

HRID 2245229Notes

Reaction equation

HRID 2245229 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])O1.Br[C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30](=[O:37])[C@H:31]([OH:36])[CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:26][CH2:25]2)[CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>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.O.CC#N.CC#N.O>[OH:36][C@H:31]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:30]([N:27]1[CH2:26][CH2:25][N:24]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[OH:15])[N:23]=2)[CH2:29][CH2:28]1)=[O:37]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 58853195HCID 58853195, compound

Product 1

HCID 135526516HCID 135526516, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent3×HCID 18373917Acetonitrile--water (1/1)Solvent2×

Conditions

Temperature
120 °C

Procedure

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (25 μL, 120/μmol), 1a (36 mg, 100 μmol), Pd(Ph3P)4 (12 mg, 10 μmol), K2CO3 (28 mg, 200 μmol), CH3CN (900 μL), and H2O(100 μL) were sealed in a microwave vessel and heated by microwave irradiation at 120° C. for 15 minutes. The reaction was filtered and purified by reverse phase HPLC to give 4. (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O(0.05% TFA). LCMS: m/z 370.1 (M+H)+ at 2.89 minutes (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O(0.05% TFA).

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by reverse phase HPLC
  3. customto give 4

Sources & evidence

ORD record
ord-f96606565ae0488fb9f0a44f041e1c0a
Source dataset
uspto-grants-2010_03
Patent number
US07683065B2

Reaction notes

Loading…