Sodium Carbonate → HCID 86653123, compound

HRID 1258567Notes

Reaction equation

HRID 1258567 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>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.C1(C)C=CC=CC=1.C(O)C.O>[CH3:23][N:22]1[C:18]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][O:9][CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:7]=2)=[N:19][N:20]=[N:21]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86653112N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 86653123HCID 86653123, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
90 °C

Procedure

In a dried and purged vessel were added N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0.536 mmol, 1 eq.), phenylboronic acid (0.072 g, 0.58 mmol, 1.1 eq.), Na2CO3 (0.119 g, 1.12 mmol, 2.1 eq.) and Tetrakis(triphenylphosphine)palladium (0.030 g, 0.027 mmol, 0.05 eq.). A mixture of solvent was added toluene/ethanol/water (4/1/1) was added and the vessel purged with argon and sealed. The reaction was heated to 90° C. for 6 hrs. After cooling, 10 ml of EtOAc were added and the solids were filtered through a “Celite” plug and washed with EtOAc. The organics were separated, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 1-(1-methyl-1H-tetrazol-5-yl)-1-phenyl-N-[(6-phenylpyridin-2-yl)methoxy]methanimine (0.192 g, 91% yield) as a colorless gum.

Workup

  1. customIn a dried
  2. custompurged vessel
  3. additionA mixture of solvent
  4. additionwas added
  5. customthe vessel purged with argon
  6. customsealed
  7. temperatureAfter cooling
  8. addition10 ml of EtOAc were added
  9. filtrationthe solids were filtered through a “Celite” plug
  10. washwashed with EtOAc
  11. customThe organics were separated
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated
  14. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-65c38164710f4ea8bc3042fbc9b07eda
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

Loading…