Dimethylformamide → HCID 71153100, compound

HRID 872245Notes

Reaction equation

HRID 872245 reaction equation
Br[C:2]1[C:3]([C:17]2[N:27]=[C:20]3[C:21]([CH3:26])=[N:22][CH:23]=[C:24]([CH3:25])[N:19]3[N:18]=2)=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[CH3:28][N:29](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[CH3:25][C:24]1[N:19]2[N:18]=[C:17]([C:3]3[C:2]([C:28]#[N:29])=[CH:7][N:6]4[CH:8]=[C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[N:10]=[C:5]4[CH:4]=3)[N:27]=[C:20]2[C:21]([CH3:26])=[N:22][CH:23]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 71153141HCID 71153141, compound

Product 1

HCID 71153100HCID 71153100, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A 2-dram pressure rated scintillation vial was charged with 2-(6-bromo-2-phenylimidazo[1,2-a]pyridin-7-yl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (20 mg, 0.048 mmol) and suspended in DMF (477 mL). To that stirring solution was added zinc cyanide (5.60 mg, 0.048 mmol). The vial was sealed and degassed using dry argon and sonication for 1 minute. Tetrakis(triphenylphosphine)palladium(0) (16.5 mg, 0.014 mmol) was then added in one portion. The vial was resealed, flushed with argon, and placed in a reaction block preheated to 90° C. After 1.25 hours, LCMS showed complete conversion of starting material to a major peak with the desired product (m/z=366 [M+H]+). Upon cooling, a solid began to form. The crude material was purified by HPLC method 10. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.55 (1H, s), 8.65 (1H, s), 8.46 (1H, s), 8.14 (1H, s), 8.09 (2H, d, J=7.28 Hz), 7.50-7.56 (2H, m), 7.40-7.46 (1H, m), 2.88 (3H, s), 2.78 (3H, s). Mass found 366 [M+H]+.

Workup

  1. customThe vial was sealed
  2. customdegassed
  3. customargon and sonication for 1 minute
  4. customflushed with argon
  5. custompreheated to 90° C
  6. temperatureUpon cooling
  7. customto form
  8. customThe crude material was purified by HPLC method 10

Sources & evidence

ORD record
ord-6a710c7084014dddad0d77bd144abb2d
Source dataset
uspto-grants-2015_03
Patent number
US08975276B2

Reaction notes

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