3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 46205883, compound

HRID 1408469Notes

Reaction equation

HRID 1408469 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[O:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:6]=2[N:7]=1.[OH:21][C:22]1[CH:23]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:25]=[CH:26][CH:27]=1>COCCOC.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>[O:18]1[CH2:19][CH2:20][N:15]([C:4]2[C:5]3[O:10][C:9]4[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=4[C:6]=3[N:7]=[C:2]([C:26]3[CH:27]=[C:22]([OH:21])[CH:23]=[CH:24][CH:25]=3)[N:3]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 2

HCID 27346233-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 58508038HCID 58508038, compound

Product 1

HCID 46205883HCID 46205883, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

Argon gas was bubbled through a mixture of 2-chloro-4-morpholinobenzofuro[3,2-d]pyrimidine (ASA66) (48.7 mg, 168 □mol, 1.0 eq) and 3-Hydroxyphenylboronic acid pinacol ester (MW 220) (148 mg, 672 □mol, 4.0 eq) in 1,2 dimethoxyethan and 2 M Na2CO3 (3:1) (4 mL) for 5 min. Dichloro 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane complex (MW 732) (3.07 mg, 4.20 □mol, 0.025 eq) was added and the reaction mixture was heated to reflux (90° C.) for 15.5 h. The red solution was cooled and diluted with EtOAc (6.5 mL). The organic solution was washed with a mixture of H2O:Na2CO3:NH4OH (conc. 32% in water)=5:4:1 (6.5 mL), then NH4Cl (sat.) and brine (2×), dried over Na2CO3, filtered and concentrated. Purification by silica gel chromatography gave a colorless solid (49 mg, 85%).

Workup

  1. additionDichloro 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane complex (MW 732) (3.07 mg, 4.20 □mol, 0.025 eq) was added
  2. temperaturethe reaction mixture was heated
  3. temperatureThe red solution was cooled
  4. washThe organic solution was washed with a mixture of H2O
  5. dry with materialNa2CO3:NH4OH (conc. 32% in water)=5:4:1 (6.5 mL), then NH4Cl (sat.) and brine (2×), dried over Na2CO3
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-331b14460b314974a8cac38fb6d4374f
Source dataset
uspto-grants-2014_12
Patent number
US08921361B2

Reaction notes

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