Cesium carbonate → 7-chloro-6-fluoro-2-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-2H-pyrazolo[4,3-b]pyridine

HRID 1522620Notes

Reaction equation

HRID 1522620 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+].Br[CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([CH2:19][CH2:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[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][CH2:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C:3]=12

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 674705117-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridine

Product 2

HCID 674696167-chloro-6-fluoro-2-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-2H-pyrazolo[4,3-b]pyridineHCID 674704897-chloro-6-fluoro-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridine (200 mg, 1.166 mmol) in DMF (5 mL), Cs2CO3 (570 mg, 1.749 mmol), and 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.194 mL, 1.282 mmol) in a sealed pressure vessel was heated at 110° C. for 3 hours. The reaction mixture was then concentrated and partitioned between water (20 mL) and EtOAc (2×50 mL). The organics were dried over Na2SO4 and evaporated to give 7-chloro-6-fluoro-2-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-2H-pyrazolo[4,3-b]pyridine and 7-chloro-6-fluoro-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazolo[4,3-b]pyridine which was used without further purification. MS [M+H] found 300.2.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between water (20 mL) and EtOAc (2×50 mL)
  3. dry with materialThe organics were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-9eb7ea348c82420dabd256b728c69a48
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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