Triethylamine → 2-Amino-5-thiophen-3-ylpyridine-3-carbaldehyde

HRID 241419Notes

Reaction equation

HRID 241419 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5](I)=[CH:4][N:3]=1.[B-](F)(F)(F)[C:12]1[CH:16]=[CH:15][S:14][CH:13]=1.[K+].C(N(CC)CC)C>C(O)C.O.C(OCC)(=O)C.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]>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 177501772-Amino-5-iodopyridine-3-carbaldehydeHCID 23677379Potassium 3-thiophenetrifluoroborate

Product 1

HCID 871848792-Amino-5-thiophen-3-ylpyridine-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
80 °C

Procedure

150 mg (0.605 mmol) of 2-amino-5-iodopyridine-3-carbaldehyde and 115 mg (0.605 mmol) of potassium 3-thiophenetrifluoroborate are suspended in 4 ml of ethanol in a nitrogen-filled reaction vessel, and 251 μl (1.814 mmol) of triethylamine and 22.1 mg (0.030 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride are added. The reaction mixture is stirred at 80° C. for 14 h under a nitrogen protective atmosphere. The reaction mixture is cooled to room temperature and diluted with water/ethyl acetate and filtered off. The organic phase is separated, and the aqueous phase is extracted a further 2× with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered, and the solvent is removed, giving 2-amino-5-thiophen-3-ylpyridine-3-carbaldehyde; HPLC-MS [M+H]+ 205.2.

Workup

  1. additionfilled
  2. additionare added
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered off
  5. customThe organic phase is separated
  6. extractionthe aqueous phase is extracted a further 2× with ethyl acetate
  7. dry with materialThe combined organic phases are dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent is removed

Sources & evidence

ORD record
ord-47aed2f093d1447581e24f4b4f9d2953
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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