Triphenylphosphine → 3-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine

HRID 1716288Notes

Reaction equation

HRID 1716288 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:34][O:35][C:36]1[C:41]([CH2:42][OH:43])=[CH:40][CH:39]=[CH:38][N:37]=1.[Br:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][C:54](O)=[CH:53][CH:52]=2)=[CH:47][CH:46]=1>C1COCC1>[Br:44][C:45]1[CH:46]=[CH:47][C:48]([C:51]2[CH:56]=[CH:55][C:54]([O:43][CH2:42][C:41]3[C:36]([O:35][CH3:34])=[N:37][CH:38]=[CH:39][CH:40]=3)=[CH:53][CH:52]=2)=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 950934-Bromo-4'-hydroxybiphenylHCID 5363146Diisopropyl azodicarboxylateHCID 10630565(2-Methoxypyridin-3-yl)methanol

Product 1

HCID 685127243-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of PPh3 (0.53 g, 2.03 mmol) and DIAD (0.4 mL, 2.03 mmol) in dry THF (3 mL) at 0° C. was added a mixture of (2-methoxy-pyridin-3-yl)-methanol (0.18 g, 1.27 mmol) from Step A and 4′-bromo-biphenyl-4-ol (0.33 g, 1.33 mmol) in dry THF (2 mL). After 1 hr, the reaction was warmed to room temperature and monitored by TLC. After the reaction was completed (˜4 h), the reaction mixture was concentrated under vacuo and then diluted with EtOAc. The precipitates were filtered. The filtrate was brought to the usual work-up. The resulting crude product was purified by chromatography (silica gel, 15% EtOAc/hexanes) to give the titled compound. MS: 370, 372 (M+H)+.

Workup

  1. additionwas added
  2. custom(˜4 h)
  3. concentrationthe reaction mixture was concentrated under vacuo
  4. additiondiluted with EtOAc
  5. filtrationThe precipitates were filtered
  6. customThe resulting crude product was purified by chromatography (silica gel, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d9b6a02ac3aa427588daf5874ea11e16
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

Loading…