Triphenylphosphine → HCID 22050982, compound

HRID 1832028Notes

Reaction equation

HRID 1832028 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:32][C:33]1[C:34](=[O:48])[N:35]([CH2:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)[C:36]([CH3:40])=[CH:37][C:38]=1[OH:39].[F:49][C:50]1[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:51]=1[CH2:52]O>CN(C=O)C>[Cl:32][C:33]1[C:34](=[O:48])[N:35]([CH2:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)[C:36]([CH3:40])=[CH:37][C:38]=1[O:39][CH2:52][C:51]1[CH:54]=[CH:55][C:56]([F:58])=[CH:57][C:50]=1[F:49]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 918672,4-Difluorobenzyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 54724229HCID 54724229, compound

Product 1

HCID 22050982HCID 22050982, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a degassed cold solution of DMF (10 mL) and PPh3 (resin, 2.2 g, 6.6 mmol) was added DEAD (1.038 mL, 6.6 mmol). The reaction mixture stirred at −10° C. for 20 minutes under nitrogen. A solution of 3-chloro-4-hydroxy-6-methyl-1-(pyridin-3-ylmethyl)pyridin-2(1H)-one (1.00 g, 4.0 mmol) and 2,4-difluorobenzylalcohol (0.66 mL, 6.0 mmol) in DMF (10 mL) was added to the resin suspension. The reaction mixture stirred at −10° C. for 30 minutes and then allowed to stir at room temperature for 1 hour. The resin was filtered and rinsed with fresh MeOH and the filtrate concentrated. The residue was dissolved in ethyl acetate and purified by flash column chromatography (5% methanol in ethyl acetate). The appropriate fractions were concentrated. 1H-NMR (CD3OD, 400 MHz) δ 8.45 (ddd, 2H, J=1.6 Hz, 1.6 Hz, 1.6 Hz), 7.61 (m, 2H), 7.41 (dd, 1H, J=4.4 Hz, 4.8 Hz), 7.02 (m, 2H), 6.55 (s, 1H), 5.43 (s, 2H), 5.29 (s, 2H), 2.41 (s, 3H); ES-HRMS m/z 377.0882/379.0840 (M+H calculated for C19H16N2O2F2Cl requires 377.0863/379.0840).

Workup

  1. stirringThe reaction mixture stirred at −10° C. for 30 minutes
  2. stirringto stir at room temperature for 1 hour
  3. filtrationThe resin was filtered
  4. washrinsed with fresh MeOH
  5. concentrationthe filtrate concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. custompurified by flash column chromatography (5% methanol in ethyl acetate)
  8. concentrationThe appropriate fractions were concentrated

Sources & evidence

ORD record
ord-40c9d94a33f14accb65aa52eb001ba75
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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