Sodium Carbonate → (S)-2-(5-(3-Amino-6-methoxy-5-(trifluoromethyl)-4-vinylpyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol

HRID 574219Notes

Reaction equation

HRID 574219 reaction equation
[NH2:1][C:2]1[C:3]([C:15]2[O:19][C:18]([C@@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22])=[N:17][N:16]=2)=[N:4][C:5]([O:13][CH3:14])=[C:6]([C:9]([F:12])([F:11])[F:10])[C:7]=1Cl.[CH3:27][C:28]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[Na+].[Na+]>CC#N.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:15]2[O:19][C:18]([C@@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22])=[N:17][N:16]=2)=[N:4][C:5]([O:13][CH3:14])=[C:6]([C:9]([F:12])([F:11])[F:10])[C:7]=1[CH:27]=[CH2:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71515814(S)-2-(5-(3-amino-4-chloro-6-methoxy-5-(trifluoromethyl)pyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol

Product 1

HCID 86729605(S)-2-(5-(3-Amino-6-methoxy-5-(trifluoromethyl)-4-vinylpyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of (S)-2-(5-(3-amino-4-chloro-6-methoxy-5-(trifluoromethyl)pyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol (Ex 13.1) (160 mg, 0.393 mmol) in MeCN (1 ml) was added bis(triphenyl phosphine)palladium(II) chloride (Aldrich) (83 mg, 0.118 mmol) followed by 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (Sigma Aldrich)(0.087 ml, 0.511 mmol). 2M Sodium carbonate (0.885 ml, 1.770 mmol) was added and the resulting mixture was heated at 130° C. for 30 minutes using microwave radiation. The mixture was filtered through Celite® and washed through with EtOAc. The filtrate was diluted further with EtOAc (50 ml) and washed with sat.NaHCO3, water, brine and dried over MgSO4. Isolute Si-TMT (2,4,6-trimercaptotriazine silica, palladium scavenger) was added the mixture was stirred for 30 mins and filtered. The solvent was removed in vacuo to afford the title compound which was used without further purification;

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed through with EtOAc
  3. additionThe filtrate was diluted further with EtOAc (50 ml)
  4. washwashed
  5. dry with materialNaHCO3, water, brine and dried over MgSO4
  6. additionIsolute Si-TMT (2,4,6-trimercaptotriazine silica, palladium scavenger) was added the mixture
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ff0c4be5d1e7443697c2f2c24ced8255
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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