Sodium Carbonate → HCID 66716893, compound

HRID 2409572Notes

Reaction equation

HRID 2409572 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[S:12][C:11]3=[N:13][CH:14]=[C:15](I)[N:10]3[N:9]=2)[CH:5]=[N:4]1)[CH3:2].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.[Na+].[Na+]>O1CCOCC1.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>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[S:12][C:11]3=[N:13][CH:14]=[C:15]([C:25]4[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[C:28]([NH2:31])=[N:29][CH:30]=4)[N:10]3[N:9]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 66716941HCID 66716941, compound

Product 1

HCID 66716893HCID 66716893, compoundYield 13.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(1-Ethyl-1H-pyrazol-4-yl)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole (110 mg, 0.319 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (119 mg, 0.414 mmol, 1.3 eq), Pd(PPh3)2Cl2 (45 mg, 0.064 mmol, 0.2 eq) and 2M aq Na2CO3 (1 mL) in dioxane (3 mL) was refluxed for 2 h. The solvent was evaporated and the residue was treated with water. The suspension was filtered off and washed with Et2O. The solid was purified by column chromatography (DCM/MeOH 9:1) to afford the desired product (16 mg, 13%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=4.62 min, [M+H]+ m/z 380.1; 1H NMR (300 MHz, DMSO) δ 8.84 (s, 1H), 8.61 (s, 1H), 8.29 (d, J=2.0 Hz, 1H), 8.08 (s, 1H), 7.74 (s, 1H), 6.72 (s, 2H), 4.24 (q, J=7.3 Hz, 2H), 1.43 (t, J=7.3 Hz, 3H).

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was evaporated
  3. additionthe residue was treated with water
  4. filtrationThe suspension was filtered off
  5. washwashed with Et2O
  6. customThe solid was purified by column chromatography (DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-4932b5150d4d4a48b002b8030f73778c
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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