Potassium Carbonate → HCID 127255428, compound

HRID 1778036Notes

Reaction equation

HRID 1778036 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[C:11](=[O:18])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[NH2:12].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:14]([O:13][C:11](=[O:18])[NH:12][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 455880804,6-Dichloropyridine-3-carbonitrile

Product 1

HCID 127255428HCID 127255428, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4-dichloro-5-cyanopyridine (10g, 57.8 mmol), tert-butyl carbamate (8.2 g, 70.5 mmol), Pd(OAc)2 (0.26 g, 1.1 mmol), Xantphos (1.34 g, 2.3 mmol) and K2CO3 (12 g, 87 mmol) in THF (150 ml) was degassed 3× with nitrogen. The mixture was then heated at 70° C. for 4-5 h and monitored by chromatography until complete conversion. Following completion of the reaction, additional THF (100 ml) was added and heated the mixture at 70° C. for additional 1 h and then cooled to room temperature. The suspension was then filtered through a pad of celite to remove the solid. The filtrate was then concentrated and azeotropically distilled with ethyl acetate before filtering to give the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 10.82 (s, 1H), 8.79 (s, 1H), 8.09 (s, 1H), 1.49 (s, 9H).

Workup

  1. customwas degassed 3× with nitrogen
  2. customcompletion of the reaction, additional THF (100 ml)
  3. additionwas added
  4. temperatureheated the mixture at 70° C. for additional 1 h
  5. temperaturecooled to room temperature
  6. filtrationThe suspension was then filtered through a pad of celite
  7. customto remove the solid
  8. concentrationThe filtrate was then concentrated
  9. distillationazeotropically distilled with ethyl acetate
  10. filtrationbefore filtering

Sources & evidence

ORD record
ord-ae923a1e62874f87b548eb4f7ec46076
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…