Dimethylformamide → HCID 89938707, compound

HRID 1777956Notes

Reaction equation

HRID 1777956 reaction equation
Br[C:2]1[C:3]([CH2:9][CH3:10])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:11][N:12](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>[NH2:8][C:5]1[CH:4]=[C:3]([CH2:9][CH3:10])[C:2]([C:11]#[N:12])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 67208872HCID 67208872, compound2×

Product 1

HCID 89938707HCID 89938707, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 5-bromo-4-ethylpyridin-2-amine (intermediate 99, 110 mg, 0.55 mmol), zinc cyanide (71 mg, 0.60 mmol) and Pd(PPh3)4 (63 mg, 0.06 mmol) in DMF (1 ml) was flushed with argon and heated in a septum sealed vial at 85° C. for 18 h. The cooled reaction mixture was evaporated, preabsorbed onto isolate and purified by normal phase chromatography with a 12 g RediSep® column: eluting with a gradient from DCM to 20% MeOH in DCM. Product containing fractions were combined and evaporated to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H), 6.92 (s, br, 2H), 6.37 (s, 1H), 2.57 (q, 2H), 1.17 (t, 3H).

Workup

  1. customwas flushed with argon
  2. temperatureheated in a septum
  3. customsealed vial at 85° C. for 18 h
  4. customThe cooled reaction mixture
  5. customwas evaporated
  6. custompreabsorbed
  7. customonto isolate
  8. custompurified by normal phase chromatography with a 12 g RediSep® column
  9. washeluting with a gradient from DCM to 20% MeOH in DCM
  10. additionProduct containing fractions
  11. customevaporated

Sources & evidence

ORD record
ord-ced30227e9c64a668db09a25d84dbf6d
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…