Toluene → HCID 71184222, compound

HRID 1519225Notes

Reaction equation

HRID 1519225 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:21](OC)=[O:22])=[N:6][CH:7]=1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][OH:22])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 67452988HCID 67452988, compound

Product 1

HCID 71184222HCID 71184222, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carboxylate (0.15 g, 0.41 mmol) in 1 ml of THF at −78° C. was added 1M DIBAL-H in toluene (1.03 ml, 1.03 mmol) dropwise. After 5 min, the reaction was allowed to warm to room temperature and stirred for 4 h. Water (0.1 ml), 10% NaOH (0.1 ml) and celite were added to the reaction solution and the mixture was filtered. Washed with THF and the filtrate was dried over Na2SO4, filtered, concentrated and purified by flash chromatography (silica, 20-50% EtOAc/hexanes) to provide {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol as white solid: 1H NMR (400 MHz, CDCl3) δ 8.37 (d, J=2.5 Hz, 1H), 8.05 (m, 2H), 7.56 (dd, J=8.4, 2.5 Hz, 1H), 7.13 (m, 3H), 4.72 (d, J=6.2 Hz, 2H), 2.98 (d, J=6.2 Hz, 1H); LCMS [M+H]+=337.3.

Workup

  1. filtrationthe mixture was filtered
  2. washWashed with THF
  3. dry with materialthe filtrate was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (silica, 20-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3f164307dfdb488b938ceae8319554f4
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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