1,2-Dimethoxyethane → HCID 57933064, compound

HRID 1432566Notes

Reaction equation

HRID 1432566 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](B(O)O)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].Br[C:21]1[S:25][C:24]([CH3:26])=[N:23][C:22]=1[CH3:27].C([O-])([O-])=O.[Na+].[Na+].COCCOC>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.CCO.O>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:21]3[S:25][C:24]([CH3:26])=[N:23][C:22]=3[CH3:27])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2986285-Bromo-2,4-dimethyl-1,3-thiazoleHCID 688409298-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-3-yl boronic acid

Product 1

HCID 57933064HCID 57933064, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a microwave pressure tube is added 0.340 g (1.30 mmol) of 8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-3-yl boronic acid, 0.100 g (0.521 mmol) of 5-bromo-2,4-dimethylthiazole, 0.361 g (0.313 mmol) of Pd(PPh3)4, 0.650 mL (1.30 mmol) of 2 M aqueous Na2CO3, and 2 mL 7:3:2 DME:H2O:EtOH, and the mixture is heated at 160° C. for 40 min. Reaction is checked by MS which indicates product present. The reaction mixture is partitioned between 75 mL of ethyl acetate and 75 mL of water. The layers are separated and the aqueous is extracted 3×50 mL of ethyl acetate, dried (MgSO4), and concentrated under vacuum. The crude mixture is purified by chromatography using hexanes/ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.100 g of the product, 58% yield. MS, ES+=329.2 (M+1); 1H-NMR (DMSO-d6)=6.974 (s, 1H); 3.085-3.052 (m, 1H); 2.665 (s, 3H); 2.438 (s, 3H); 2.290 (s, 3H); 2.147 (s, 3H); 1.849-1.727 (m, 4H); 0.776-0.738 (m, 6H) ppm.

Workup

  1. customReaction
  2. customThe reaction mixture is partitioned between 75 mL of ethyl acetate and 75 mL of water
  3. customThe layers are separated
  4. extractionthe aqueous is extracted 3×50 mL of ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customThe crude mixture is purified by chromatography
  8. additionThe product containing fractions

Sources & evidence

ORD record
ord-86db2408fe66436ea402cc69a97b7ae4
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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