Dimethylformamide → HCID 53251307, compound

HRID 509619Notes

Reaction equation

HRID 509619 reaction equation
Br[C:2]1[N:3]=[C:4]([CH:8]=[CH:9][C:10]2[N:11]=[C:12]3[N:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[N:13]3[CH:20]=2)[N:5]([CH3:7])[CH:6]=1.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)CCC.CN(C=O)C.C(=O)(O)[O-].[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.C1COCC1>[CH3:19][C:14]1[N:13]2[CH:20]=[C:10](/[CH:9]=[CH:8]/[C:4]3[N:5]([CH3:7])[CH:6]=[C:2]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)[N:3]=3)[N:11]=[C:12]2[N:17]=[C:16]([CH3:18])[CH:15]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 67257062HCID 67257062, compound

Product 1

HCID 53251307HCID 53251307, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

A glass vial was charged with 2-[2-(4-Bromo-1-methyl-1H-imidazol-2-yl)-vinyl]-5,7-dimethyl-imidazo[1,2-a]pyrimidine (150 mg, 0.45 mmol), tributyl-(2-thienyl)-stannane (226 μL, 0.67 mmol), DMF (4 mL) and the slurry was deoxygenated by bubbling argon through then tetrakis(triphenylphosphine)palladium(0) (26 mg, 0.05 mmol) was added and the vessel sealed and heated in a microwave reactor at 160° C. for 30 minutes. THF (15 mL) was added followed by saturated sodium bicarbonate solution (25 mL). The organic layer was separated and the aqueous extracted with THF (15 mL). The combined extracts were dried over Na2SO4, filtered and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel (EtOAc:Et3N, 95:5) to yield the title compound (60 mg, 40%) as a light brown solid. 1H NMR (500 MHz, CDCl3): δ 8.10 (s, 1H), 7.58 (s, 1H), 7.49-7.41 (m, 1H), 7.39-7.31 (m, 2H), 7.29-7.25 (m, 1H), 7.18-7.12 (m, 1H), 6.83 (s, 1H), 3.79 (s, 3H), 2.60 (s, 3H), 2.49 (s, 3H). LCMS (MH+): m/z=336.4, tR (minutes, method A)=0.51

Workup

  1. customthe slurry was deoxygenated
  2. additionwas added
  3. customthe vessel sealed
  4. customThe organic layer was separated
  5. extractionthe aqueous extracted with THF (15 mL)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customthe volatiles removed in vacuo
  9. customThe residue was purified by column chromatography on silica gel (EtOAc:Et3N, 95:5)

Sources & evidence

ORD record
ord-34da0d596cbf4c1a9ba9a4066f68323b
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

Loading…