Cesium fluoride → HCID 89350931, compound

HRID 1497314Notes

Reaction equation

HRID 1497314 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[CH:5]=[C:4]([Cl:18])[N:3]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[N:25][CH:26]=1.[F-].[Cs+]>O1CCOCC1.O>[Cl:18][C:4]1[N:3]=[C:2]([C:23]2[CH:24]=[N:25][CH:26]=[C:21]([C:20]([F:31])([F:30])[F:19])[CH:22]=2)[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[CH:5]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 45158900[5-(Trifluoromethyl)pyridin-3-yl]boronic acidHCID 89350889(2,6-Dichloro-pyrimidin-4-yl)-(2,4-difluoro-benzyl)-amine

Product 1

HCID 89350931HCID 89350931, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of (2,6-Dichloro-pyrimidin-4-yl)-(2,4-difluoro-benzyl)-amine (1 g, 0.0034 mol) and 5-trifluoromethylpyridine-3-boronic acid (0.726 g, 0.0038 mol) were taken in dioxane:water (20:5) ml and to this CsF (2.1 g, 0.0138 mol) was added and degassed. Then bis-triphenylphosphine-palladium(II) chloride (0.24 g, 0.00034 mol) was added and degassed. The mixture was stirred at 60° C. for 12 hrs. The reaction was cooled to room temperature diluted with water (50 ml) and ethyl acetate (100 ml). After standard work-up, the residue was purified by column chromatography to get compound as white solid.

Workup

  1. customdegassed
  2. customdegassed
  3. temperatureThe reaction was cooled to room temperature
  4. additiondiluted with water (50 ml) and ethyl acetate (100 ml)
  5. customAfter standard work-up, the residue was purified by column chromatography
  6. customto get compound as white solid

Sources & evidence

ORD record
ord-5f6a859c98cb4b198eebfdd35b5928bc
Source dataset
uspto-grants-2015_12
Patent number
US09199962B2

Reaction notes

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