Triphenylphosphine → HCID 68902396, compound

HRID 1785732Notes

Reaction equation

HRID 1785732 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:27]([F:30])([F:29])[F:28])=[C:10]([CH2:14][O:15][CH:16]3[CH2:19][N:18]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.B1([C:37]2[CH:42]=[CH:41][CH:40]=[N:39][CH:38]=2)OCCCO1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:39]1[CH:40]=[CH:41][CH:42]=[C:37]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:9]([C:27]([F:29])([F:30])[F:28])=[C:10]([CH2:14][O:15][CH:16]4[CH2:19][N:18]([C:20]([NH:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[CH2:17]4)[CH:11]=[CH:12][CH:13]=3)=[CH:6][CH:7]=2)[CH:38]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 68903769HCID 68903769, compound

Product 1

HCID 68902396HCID 68902396, compoundYield 8.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of aryl iodide (191) (100 mg, 0.19 mmol), pyridine-3-boronic acid 1,3-propanediol cyclic ester (61 mg, 0.38 mmol), palladium acetate (4 mg, 0.019 mmol) and triphenylphosphine (10 mg, 0.38 mmol) in tetrahydrofuran (10 mL) was added sodium bicarbonate (10 mL, saturated aqueous). The reaction mixture was heated to reflux (65° C.) for 4 h, cooled, filtered and partitioned between water (20 mL) and ethyl acetate (20 mL). The organic phase was separated and washed with brine (20 mL), dried (Na2SO4), filtered and the solvent removed under reduced pressure to afford the crude product as a yellow oil. Purification by silica gel chromatography (50% ethyl acetate/iso-hexane eluant) followed by preparative HPLC gave the title compound (194) as a colourless gum (7.7 mg, 8.5% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled
  3. filtrationfiltered
  4. custompartitioned between water (20 mL) and ethyl acetate (20 mL)
  5. customThe organic phase was separated
  6. washwashed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customto afford the crude product as a yellow oil
  11. customPurification by silica gel chromatography (50% ethyl acetate/iso-hexane eluant)

Sources & evidence

ORD record
ord-7847d0a589b14840a0668750baef4bc6
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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