Potassium Carbonate → HCID 46941132, compound

HRID 2409587Notes

Reaction equation

HRID 2409587 reaction equation
I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)(=[O:18])=[O:17])[CH:11]=3)=[N:8]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[C:35]([C:40]([F:43])([F:42])[F:41])[C:36]([NH2:39])=[N:37][CH:38]=2)O1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C(Cl)Cl.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]>[N:19]1([S:16]([C:12]2[CH:11]=[C:10]([C:7]3[S:6][C:5]4=[N:4][CH:3]=[C:2]([C:33]5[CH:34]=[C:35]([C:40]([F:43])([F:42])[F:41])[C:36]([NH2:39])=[N:37][CH:38]=5)[N:9]4[N:8]=3)[CH:15]=[CH:14][CH:13]=2)(=[O:18])=[O:17])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 66717221HCID 66717221, compound

Product 1

HCID 46941132HCID 46941132, compoundYield 22.9%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-Iodo-2-[3-(morpholine-4-sulfonyl)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazole (18 mg, 0.053 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (20 mg, 0.068 mmol), PdCl2(dppf) (9 mg, 0.011 mmol) and sat K2CO3 (0.22 mL) in DME (0.5 mL) was heated under microwave irradiation at 120° C. for 30 min. The reaction mixture was cooled, diluted with DCM and washed with water. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (5% MeOH in DCM) to give the desired product (6.2 mg, 19%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.13 min, [M+H]+ m/z 511.1; 1H NMR (300 MHz, DMSO) δ 8.75 (s, 1H), 8.29 (s, 1H), 8.20 (d, J=7.6 Hz, 1H), 8.10 (s, 1H), 7.83 (m, 2H), 7.72 (s, 1H), 6.65 (s, 2H), 3.53 (m, 4H), 2.84 (m, 4H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-6f8403e5acd4444bb28be1b018703317
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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