HCID 131732909, compound → HCID 89635862, compound

HRID 1476777Notes

Reaction equation

HRID 1476777 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27]C)=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]3[CH:14]=2)[CH:7]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]3[CH:14]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 131732909HCID 131732909, compound

Product 1

HCID 89635862HCID 89635862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-ethyl 5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (synthesized similar to that of Int-84 using intermediate 41) (1.2 g, 3.13 mmol) in 25 mL of DCM, 1.0M Borontribromide (15.6 ml, 39.2 g, 15.65 mmol) was added at −70° C. and stirred at −70° C. to room temperature during 16 h. Reaction mass was quenched with 5 mL of ice cooled water and stirred for 15 min. The reaction mixture was diluted with DCM (50 mL) and the organic layer was washed with water followed by brine. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford of the title compound (Int-76) as off white solid. MS (ESI): m/z 370.3 (M+H).

Workup

  1. addition1.0M Borontribromide (15.6 ml, 39.2 g, 15.65 mmol) was added at −70° C.
  2. customReaction mass
  3. customwas quenched with 5 mL of ice
  4. temperaturecooled water
  5. stirringstirred for 15 min
  6. additionThe reaction mixture was diluted with DCM (50 mL)
  7. washthe organic layer was washed with water
  8. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f221624feb78456fadb67629b27046af
Source dataset
uspto-grants-2016_08
Patent number
US09402833B2

Reaction notes

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