Sodium Carbonate → HCID 86653121, compound

HRID 1258565Notes

Reaction equation

HRID 1258565 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[N:21]([CH3:22])[N:20]=[N:19][N:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.[CH:23](/B(O)O)=[CH:24]\[CH2:25][CH2:26][CH2:27][CH3:28].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>[CH:23](/[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[N:21]([CH3:22])[N:20]=[N:19][N:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)=[CH:24]\[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5326225B-(1E)-1-Hexenylboronic acidHCID 86649974N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 86653121HCID 86653121, compoundYield 84.3%

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-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0.527 mmol, 1 eq.), (1E)-hex-1-en-1-ylboronic acid (0.074 g, 0.58 mmol, 1.1 eq.), Na2CO3 (0.117 g, 1.107 mmol, 2.1 eq.) and Tetrakis(triphenylphosphine)palladium (0.030 g, 0.026 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 N-({2-[(1E)-hex-1-en-1-yl]-1,3-thiazol-4-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.170 g, 80% 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-15db82d32a164ababcbea4434b1425b7
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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