5-bromo-1-(4-fluorophenyl)-1H-indazole → HCID 24958372, compound

HRID 244460Notes

Reaction equation

HRID 244460 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[N:6]=[CH:5]2.[Li]CCCC.[CH2:23]([N:26]1[C:34]2[C:33](=[O:35])[N:32]([CH3:36])[CH:31]=[N:30][C:29]=2[C:28]([C:37](=[O:42])[C:38]([F:41])([F:40])[F:39])=[CH:27]1)[CH:24]=[CH2:25]>C1COCC1>[CH2:23]([N:26]1[C:34]2[C:33](=[O:35])[N:32]([CH3:36])[CH:31]=[N:30][C:29]=2[C:28]([C:37]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:6]=[CH:5]3)([OH:42])[C:38]([F:41])([F:39])[F:40])=[CH:27]1)[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 468307945-bromo-1-(4-fluorophenyl)-1H-indazoleHCID 59437234HCID 59437234, compoundHCID 178418339Butyllithium

Product 1

HCID 24958372HCID 24958372, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-1H-indazole (94 mg, 0.32 mmol, 1.1 equiv.) in 1.5 mL of THF was added n-BuLi (2.5 M in hexanes, 0.13 ml, 0.32 mmol, 1.1 equiv.) followed by a chilled (−78° C.) solution of 5-allyl-3-methyl-7-(2,2,2-trifluoro-acetyl)-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one (83 mg, 0.29 mmol, 1 equiv.) in 1 mL of THF. After 15 minutes, the mixture was quenched with water, warmed to room temperature, diluted with brine, and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hex (0-60% gradient) to provide 44 mg (30%) of the title compound as a yellow foam. MS m/z 498.31 (MH+).

Workup

  1. customthe mixture was quenched with water
  2. additiondiluted with brine
  3. extractionextracted with EtOAc
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-27b304344fc646e09713fc487f08c26a
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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