Dichloromethane → HCID 66716988, compound

HRID 2409574Notes

Reaction equation

HRID 2409574 reaction equation
I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:15]=3[CH3:16])=[N:8]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[C:28]([NH2:31])=[N:29][CH:30]=2)O1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:16][C:15]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:7]1[S:6][C:5]2=[N:4][CH:3]=[C:2]([C:25]3[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[C:28]([NH2:31])=[N:29][CH:30]=3)[N:9]2[N:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 66717033HCID 66717033, compound

Product 1

HCID 66716988HCID 66716988, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-Iodo-2-(4-methyl-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazole (18 mg, 0.053 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (20 mg, 0.068 mmol, 1.3 eq), Pd(PPh3)2Cl2 (9 mg, 0.011 mmol, 0.2 eq) and sat aq K2CO3 (0.22 mL) in DME (0.5 mL) was heated under microwave irradiation at 120° C. for 30 min. On cooling, DCM was added and the mixture was washed with water. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (DCM/MeOH 95:5) to afford the desired product (8 mg, 40%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=4.32 min, [M+H]+ m/z 377.1; 1H NMR (300 MHz, CDCl3) δ 8.80 (s, 1H), 8.70 (s, 1H), 8.55 (d, J=5.0 Hz, 1H), 8.31 (s, 1H), 7.56 (s, 1H), 7.28 (d, J=5.0 Hz, 1H), 5.39 (s, 2H), 2.63 (s, 3H).

Workup

  1. temperatureOn cooling
  2. washthe mixture was washed with water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-20e5b4596da64386b2098e0f37a6cd1f
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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