Triphenylphosphine → HCID 22050197, compound

HRID 1832019Notes

Reaction equation

HRID 1832019 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH2:32]([N:39]1[C:44]([CH3:45])=[CH:43][C:42]([OH:46])=[C:41]([Br:47])[C:40]1=[O:48])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[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>[CH2:32]([N:39]1[C:44]([CH3:45])=[CH:43][C:42]([O:46][CH2:52][C:51]2[CH:54]=[CH:55][C:56]([F:58])=[CH:57][C:50]=2[F:49])=[C:41]([Br:47])[C:40]1=[O:48])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 918672,4-Difluorobenzyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 54724226HCID 54724226, compound

Product 1

HCID 22050197HCID 22050197, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a degassed cold solution of DMF (10 mL) and PPh3 (resin, 0.93 g, 2.75 mmol) was added DEAD (0.44 mL, 2.75 mmol). The reaction mixture stirred at −10° C. for 20 minutes under nitrogen. A solution of 1-benzyl-3-bromo-4-hydroxy-6-methylpyridin-2(1H)-one (0.62 g, 2.1 mmol) and 2,4-difluorobenzylalcohol (0.283 mL, 2.5 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 was concentrated. The residue was dissolved in ethyl acetate and purified by flash column chromatography (ethyl acetate/hexane 1:1 v/v). The appropriate fractions were concentrated. 1H-NMR (CD3OD, 400 MHz) δ 7.62 (m, 1H), 7.31 (m, 3H), 7.1 (d, 2H, J=7.2 Hz), 7.02 (t, 2H, J=8.6 Hz), 6.48 (s, 1H), 5.42 (s, 2H), 5.28 (s, 2H), 2.34 (s, 3H); ES-HRMS m/z 420.0399/422.0380 (M+H calculated for C20H17NO2F2Br requires 420.0405/422.0387).

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 was concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. custompurified by flash column chromatography (ethyl acetate/hexane 1:1 v/v)
  8. concentrationThe appropriate fractions were concentrated

Sources & evidence

ORD record
ord-6985eb7a4bba44bcb4b9db7af9355ac1
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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