Hexane → 8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-3-yl boronic acid

HRID 1432565Notes

Reaction equation

HRID 1432565 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](I)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C([Li])(C)(C)C.[B:23](OC)([O:26]C)[O:24]C.CCCCCC>C1COCC1.CC(=O)OCC>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([B:23]([OH:26])[OH:24])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8470Trimethyl borateHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418306HCID 178418306, compound

Product 1

HCID 688409298-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-3-yl boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

In an oven dried nitrogen purged 3 neck 50 mL round bottom flask, 1.00 g (2.91 mmol) of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine in 60 mL of dry THF is cooled to −78° C. 4.12 mL (7.00 mmol) of 1.7 M tert-butyllithium in hexanes is added and reaction is stirred at −78° C. for 1 hour. 0.818 mL (7.30 mmol) of trimethyl borate is added and reaction is followed by MS and TLC (1:1 Hexane:EA) Indication of product is observed by mass spectrum. The reaction is allowed to stir for an additional hour, quenched with 1 N hydrochloric acid, and diluted with ethyl acetate. The organic layer is separated, and the aqueous layer is extracted three times with 100 mL of ethyl acetate. The extracts are combined, dried over MgSO4, filtered, and concentrated. The reaction residue is triturated in hexanes and a solid is filter off. MS, ES+=262.2 (M+1).

Workup

  1. customreaction
  2. customreaction
  3. stirringto stir for an additional hour
  4. customquenched with 1 N hydrochloric acid
  5. additiondiluted with ethyl acetate
  6. customThe organic layer is separated
  7. extractionthe aqueous layer is extracted three times with 100 mL of ethyl acetate
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe reaction residue is triturated in hexanes
  12. filtrationa solid is filter off

Sources & evidence

ORD record
ord-4be07f75a73a4da092dfd88a0d794e52
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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