Allyl bromide → HCID 68739064, compound

HRID 2261265Notes

Reaction equation

HRID 2261265 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[NH:6][C:5]2[N:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])[N:10]=[CH:11][C:4]=2[CH:3]=1.[H-].[Na+].[Br-].[Li+].Br[CH2:25][CH:26]=[CH2:27]>COCCOC.CN(C=O)C>[CH2:27]([N:6]1[C:7](=[O:8])[C:2]([Br:1])=[CH:3][C:4]2[CH:11]=[N:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])[C:5]1=2)[CH:26]=[CH2:25]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 135741657HCID 135741657, compound

Product 1

HCID 68739064HCID 68739064, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5-bromo-1-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (1.05 g, 3.22 mmol) in DME (10 mL) and DMF (0.9 mL) at 0° C. was treated with NaH (116 mg, 4.8 mmol). After stirring for 20 min at RT, lithium bromide (1.67 g, 19.32 m mol) was added and the reaction mixture was allowed to stir for 1 h at RT before addition of 3-bromoprop-1-ene (0.28 ml, 3.22 mmol). The mixture was allowed to stir at 40° C. for 18 h. The mixture was quenched with brine and extracted with 2×30 mL EtOAc. The combined EtOAc layers were washed with brine, dried and concentrated. Purification on the ISCO (40 g column, 10-80% EtOAc in Hexanes) afforded 7-allyl-5-bromo-1-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one as a tan amorphous solid. MS (ESI, pos.ion) m/z: 365.9/367.9 (M+1).

Workup

  1. stirringto stir at 40° C. for 18 h
  2. customThe mixture was quenched with brine
  3. extractionextracted with 2×30 mL EtOAc
  4. washThe combined EtOAc layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customPurification on the ISCO (40 g column, 10-80% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-eff7cdf45e2c40db98d26918dbb96aa4
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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