HCID 57618495, compound → HCID 57618482, compound

HRID 1690703Notes

Reaction equation

HRID 1690703 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=O)=[CH:6][C:5]=1[C:14]([OH:16])=[O:15])([O-:3])=[O:2].Cl.[CH2:18]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH:34]N)[C:29]=2[F:36])=[CH:24][CH:23]=1)[CH2:19][CH2:20][CH3:21]>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[CH2:18]([C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]3[C:9]4[CH2:8][C:7]5[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:14]([OH:16])=[O:15])[CH:6]=5)[C:10]=4[NH:34][C:30]=3[C:29]=2[F:36])=[CH:26][CH:27]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 57618495HCID 57618495, compoundHCID 66904900HCID 66904900, compound

Product 1

HCID 57618482HCID 57618482, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

A sealable reaction vial was charged with 6-nitro-1-oxo-indan-5-carboxylic acid (26 mg, 0.12 mmol), (4′-Butyl-2-fluoro-biphenyl-3-yl)-hydrazine hydrochloride (example 78, step 1) (25 mg, 0.12 mmol), zinc (II) chloride (24 mg, 0.18 mmol), and acetic acid (1.5 mL), sealed, and heated to 105° C. overnight. Reaction was then cooled to RT, concentrated in vacuo, and purified by UV-triggered HPLC to afford 22 mg (41%) of 7-(4-Butyl-phenyl)-6-fluoro-3-nitro-5,10-dihydro-indeno[1,2-b]indole-2-carboxylic acid; LC/MS calculated for [M+H]+ C26H21FN2O4: 445.1, found: 445.1.

Workup

  1. customA sealable reaction
  2. customsealed
  3. customReaction
  4. temperaturewas then cooled to RT
  5. concentrationconcentrated in vacuo
  6. custompurified by UV-triggered HPLC

Sources & evidence

ORD record
ord-da66b97f13884d6ba858c0c3799ce732
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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