Potassium Carbonate → HCID 66717247, compound

HRID 2409591Notes

Reaction equation

HRID 2409591 reaction equation
I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:11]=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=3)=[N:8]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]([C:33]([F:36])([F:35])[F:34])[C:29]([NH2:32])=[N:30][CH:31]=2)O1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][O:16][C:14]1[CH:15]=[C:10]([C:7]2[S:6][C:5]3=[N:4][CH:3]=[C:2]([C:26]4[CH:27]=[C:28]([C:33]([F:36])([F:35])[F:34])[C:29]([NH2:32])=[N:30][CH:31]=4)[N:9]3[N:8]=2)[CH:11]=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 66717025HCID 66717025, compound

Product 1

HCID 66717247HCID 66717247, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-Iodo-2-(5-methoxy-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazole (26 mg, 0.073 mmol, 1.0 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) -3-trifluoromethyl-pyridin-2-ylamine (27 mg, 0.096 mmol, 1.3 eq), PdCl2(dppf) (12 mg, 0.015 mmol, 0.2 eq), sat. K2CO3 (0.5 mL) in DME (4 mL) was heated under microwave irradiation at 120° C. for 30 min. The solvent was removed and the residue was diluted with DCM and washed with H2O and brine. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography (Isolute Si II; MeOH in DCM, 0 to 3%) to give the desired product (12 mg, 42%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=4.76 min, [M+H]+ m/z 393.0; 1H NMR (300 MHz, DMSO) δ 8.87 (d, J=1.8 Hz, 1H), 8.75 (d, J=1.7 Hz, 1H), 8.53 (d, J=2.8 Hz, 1H), 8.38 (d, J=2.0 Hz, 1H), 7.85 (m, 2H), 6.76 (s, 2H), 3.96 (s, 3H).

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with DCM
  3. washwashed with H2O and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (Isolute Si II; MeOH in DCM, 0 to 3%)

Sources & evidence

ORD record
ord-43565351b2004ddbadde5d7837d626ce
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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