Sodium Carbonate Decahydrate → 4-(2-Aminopyridin-3-yl)phenol

HRID 1748006Notes

Reaction equation

HRID 1748006 reaction equation
O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+].[Si]([O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(C(C)(C)C)(C)C.Br[C:35]1[C:36]([NH2:41])=[N:37][CH:38]=[CH:39][CH:40]=1>COCCOC.O.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>[NH2:41][C:36]1[C:35]([C:28]2[CH:27]=[CH:26][C:25]([OH:24])=[CH:30][CH:29]=2)=[CH:40][CH:39]=[CH:38][N:37]=1

Participants

7

Reactant 3

HCID 151402Sodium Carbonate DecahydrateHCID 8177002-Amino-3-bromopyridineHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 667484774-(2-Aminopyridin-3-yl)phenolYield 86.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of sodium carbonate decahydrate (86.0 g), tetrakis(triphenylphosphine)palladium(0) (7.76 g), (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (40 g) and 3-bromopyridin-2-amine (26.9 g) in DME (500 mL) and water (50 mL) was stirred at 90° C. for 24 hr. After cooling to room temperature, the aqueous layer was removed. The organic layer was filtered with NH-silica gel cartridge, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was recrystallized from EtOAc-IPE to give the title compound (25.0 g) as a pale yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe aqueous layer was removed
  3. filtrationThe organic layer was filtered with NH-silica gel cartridge
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was recrystallized from EtOAc-IPE

Sources & evidence

ORD record
ord-c3dfd2fdb8464484aedecd4cfbc1ec4d
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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