Sodium Carbonate → HCID 57933030, compound

HRID 1432569Notes

Reaction equation

HRID 1432569 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20](Br)=[N:19][C:18]=3[CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[F:24][C:25]([F:37])([F:36])[O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=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.C(O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([C:30]4[CH:29]=[CH:28][C:27]([O:26][C:25]([F:24])([F:36])[F:37])=[CH:32][CH:31]=4)=[N:19][C:18]=3[CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 68840065HCID 68840065, compound

Product 1

HCID 57933030HCID 57933030, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

To a microwave pressure tube is added 0.100 g (0.254 mmol) of 8-(1-ethyl-propyl)-3-[2-bromo-4-methyl-5-thiazolyl]-2,6-dimethyl-imidazo[1,2-b]pyridazine, 0.157 g (0.762 mmol) of 4-(trifluoromethoxy)benzene boronic acid, 0.147 g (0.127 mmol) of Pd(PPh3)4, 0.381 mL (0.762 mmol) of 2 M aqueous sodium carbonate, and 2 mL Ethanol. The reaction mixture is heated in the microwave at 160° C. for up to 1 hour. The reaction mixture is partitioned between 50 mL of ethyl acetate and 50 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 2% methanol in dichloromethane as a solvent system. The product containing fractions are combined to obtain 0.085 g of the product, 70% yield. MS, ES+=475.2 (M+1); 1H-NMR (DMSO-d6)=8.134-8.112 (d, 2H); 7.553-7.532 (d, 2H); 7.059 (s, 1H); 3.142-3.113 (m, 1H); 2.500 (s, 3H); 2.399 (s, 3H); 2.330 (s, 3H); 1.907-1.782 (m, 4H); 0.827-0.791 (m, 6H) ppm.

Workup

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

Sources & evidence

ORD record
ord-2bdc1e4550364bfdb0420f9a37c91173
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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