Triethylamine → HCID 68539179, compound

HRID 1446697Notes

Reaction equation

HRID 1446697 reaction equation
Br[C:2]1[C:3]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:13][N:14]([CH3:19])[C:15](=[O:18])[CH:16]=[CH2:17].C(N(CC)CC)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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[N:6]=[CH:7][C:2]([CH:17]=[CH:16][C:15]([N:14]([CH3:19])[CH3:13])=[O:18])=[C:3]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 17587N,N-DimethylacrylamideHCID 68539435HCID 68539435, compound

Product 1

HCID 68539179HCID 68539179, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

De-gas a mixture of 5-bromo-4-tert-butyl-pyridin-2-ylamine (330 mg, 1.4 mol), N,N-dimethylacrylamide (0.22 mL, 2.1 mmol), triethylamine (0.4 mL, 2.1 mmol) in toluene (4 mL) while purging with nitrogen for 3 minutes. Add palladium(II)acetate (60 mg, 0.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (690 mg, 0.6 mmol) under nitrogen. Heat the reaction overnight in sealed vessel at 120° C. Cool the mixture to room temperature, filter through Celite® and concentrate. Purification by silica gel column chromatography (100% DCM to 3% MeOH in DCM) to yield the title compound (81% yield). LCMS (ES), m/z 248 (M+1).

Workup

  1. customDe-gas
  2. customwhile purging with nitrogen for 3 minutes
  3. temperatureHeat
  4. customthe reaction overnight in sealed vessel at 120° C
  5. filtrationfilter through Celite®
  6. concentrationconcentrate
  7. customPurification by silica gel column chromatography (100% DCM to 3% MeOH in DCM)

Sources & evidence

ORD record
ord-efe0649b225f48f6ba0d22fe2c827b39
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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