Water → 1-(7-chloro-6-fluoro-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropan-2-ol

HRID 1522631Notes

Reaction equation

HRID 1522631 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:19][C:20]([CH3:23])([OH:22])[CH3:21].O>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])[N:11]=2)[N:5]=[CH:6][C:7]=1[F:8].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[CH:9]=[N:10][N:11]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])[C:3]=12

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 684091-Chloro-2-methylpropan-2-olHCID 674705117-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridine

Product 2

HCID 674695301-(7-chloro-6-fluoro-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropan-2-olHCID 674704651-(7-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridin-1-yl)-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 7-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridine (300 mg, 1.749 mmol) in DMF (5 mL) was added Cs2CO3 (855 mg, 2.62 mmol) and 1-chloro-2-methylpropan-2-ol (209 mg, 1.924 mmol) and the mixture was heated at 110° C. for 2 hours. Water (20 mL) was then added and the mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated to give 1-(7-chloro-6-fluoro-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropan-2-ol and 1-(7-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridin-1-yl)-2-methylpropan-2-ol which were used i without further purification. MS [M+H] found 244.2.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-262cbef6c9c1499cb6ec8f6dafec33b9
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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