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5-bromo-1-(4-fluorophenyl)-1H-indazole → 1-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 244436
Notes
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Reaction equation

HRID 244436 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]([O:25][C:26]([C:28]1[N:29]([CH2:39][CH:40]=[CH2:41])[CH:30]=[C:31]([C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])[CH:32]=1)=[O:27])[CH3:24]>C1COCC1>[CH2:23]([O:25][C:26]([C:28]1[N:29]([CH2:39][CH:40]=[CH2:41])[CH:30]=[C:31]([C:33]([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:38])[C:34]([F:36])([F:35])[F:37])[CH:32]=1)=[O:27])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 468307945-bromo-1-(4-fluorophenyl)-1H-indazoleHCID 594372701-allyl-4-(2,2,2-trifluoroacetyl)-1H-pyrrole-2-carboxylic acid ethyl esterHCID 178418339Butyllithium

Product 1

HCID 249590981-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid ethyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-1H-indazole (2.0 g, 6.8 mmol, 1.2 equiv.) in 20 mL of THF was added n-BuLi (2.5 mL, 6.2 mmol, 1.1 equiv.) followed by a chilled (−78° C.) solution of 1-allyl-4-(2,2,2-trifluoroacetyl)-1H-pyrrole-2-carboxylic acid ethyl ester (1.6 g, 5.7 mmol, 1.0 equiv.) in 3 mL of THF in one portion. After 30 minutes, the mixture was quenched with water, warmed to room temperature, diluted with brine, and extracted with EtOAc. The combined organics were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (5-30% EtOAc-hexanes) to provide 890 mg (32%) of the title compound as a pale orange solid. MS m/z 488.30 (MH+).

Workup

  1. customthe mixture was quenched with water
  2. additiondiluted with brine
  3. extractionextracted with EtOAc
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (5-30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-d1584bbe2e8e471aab5d2d64c44a349a
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658637B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes