Sodium Hydroxide → HCID 123348954, compound

HRID 1753067Notes

Reaction equation

HRID 1753067 reaction equation
[CH2:1]([O:3][C:4]#[CH:5])[CH3:2].[B]1OC2C(=CC=CC=2)O1.[F:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20](I)[C:21]=1[NH2:22].[OH-].[Na+]>C1COCC1.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>[CH2:4]([O:3][CH:1]=[CH:2][C:20]1[CH:19]=[N:18][CH:17]=[C:16]([F:15])[C:21]=1[NH2:22])[CH3:5]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61239Ether, ethyl ethynylHCID 6327445BenzcatechinboraneHCID 73553743HCID 73553743, compound

Product 1

HCID 123348954HCID 123348954, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Ethoxyacetylene (7.9 mL, 56.4 mmol) was cooled to 0° C. and a solution of catecholborane (6.1 g, 50.8 mmol) in THF (90 mL) was added slowly. The reaction was allowed to warm to room temperature over 2 hours followed by heating to reflux for 2 hours. The reaction was cooled and 3-fluoro-5-iodo-pyridin-4-ylamine (Preparation 64, 7 g, 29.4 mmol) was added as a solution in THF (20 mL). After purging with nitrogen for 20 minutes, NaOH powder (3.52 g, 88 mmol) and Pd(PPh3)4 (1 g, 0.88 mmol) were added and the reaction heated to reflux for 20 hours. The reaction was filtered through celite, washed with EtOAc, the organic layer collected, washed with brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 50% EtOAc in hexane to afford the title compound (3.59 g)

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. customAfter purging with nitrogen for 20 minutes
  5. temperaturethe reaction heated
  6. temperatureto reflux for 20 hours
  7. filtrationThe reaction was filtered through celite
  8. washwashed with EtOAc
  9. customthe organic layer collected
  10. washwashed with brine
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified
  14. washeluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-299df59c37a9466481dc6c0b9800ee36
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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