Triphenylphosphine → HCID 89924328, compound

HRID 1505674Notes

Reaction equation

HRID 1505674 reaction equation
[NH:1]1[CH:5]=[C:4]([B:6]2[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]2)[CH:3]=[N:2]1.[F:15][CH2:16][CH:17](O)[CH2:18][F:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:15][CH2:16][CH:17]([N:2]1[CH:3]=[C:4]([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:13])([CH3:12])[O:14]2)[CH:5]=[N:1]1)[CH2:18][F:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 679851,3-Difluoro-2-propanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 89924328HCID 89924328, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Pyrazole-4-boronic acid pinacol ester (6.6 g, 34 mmol, 1 eq.) in dry THF (150 mL) was added 1,3-Difluoro-2-propanol (5.1 g, 51 mmol, 1.5 eq.) followed by triphenylphosphine (13.5 g, 51 mmol, 1.5 eq.) and Diisopropyl azodicarboxylate (10.5 g, 51 mmol, 1.5 eq.) at 0° C. under nitrogen atmosphere. After the addition, the reaction mixture was stirred at RT for 48 h. The reaction mixture was concentrated under vacuum and the residue was solubilized in EtOAc, washed with water (three times), dried over sodium sulfate, filtered and concentrated. The crude product was redissolved in EtOAc and Pet. Ether was added. The precipitate obtained was filtered off and the filtrate concentrated under reduced pressure to give the title compound as a oil (contaminated with triphenyl phosphine oxide).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. washwashed with water (three times)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude product was redissolved in EtOAc
  8. additionPet. Ether was added
  9. customThe precipitate obtained
  10. filtrationwas filtered off
  11. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d39c87103cff4f619bd229020a0c2fd0
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

Loading…