Heptane → HCID 86100668, compound

HRID 2235093Notes

Reaction equation

HRID 2235093 reaction equation
C[Al](C)C.CCCCCCC.[NH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=1.C[O:26][C:27]([C:29]1[CH:37]=[C:36]2[C:32]([CH:33]=[CH:34][NH:35]2)=[CH:31][CH:30]=1)=O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>O1CCOCC1.ClCCl>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([NH:12][C:27]([C:29]2[CH:37]=[C:36]3[C:32]([CH:33]=[CH:34][NH:35]3)=[CH:31][CH:30]=2)=[O:26])=[CH:14][C:15]=1[C:21]([F:22])([F:23])[F:24])#[N:18]

Participants

8

Reactant 5

HCID 8900HeptaneHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 639844Methyl indole-6-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 86100668HCID 86100668, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A 2 N trimethylaluminium solution in heptane (30.8 mmol, 15.41 mL, 3 equiv.) was added dropwise over 10 minutes to a solution of 4-amino-2-trifluoromethylbenzonitrile (30.8 mmol, 5.7 g, 3 equiv.) in dry dioxane (20 mL). The reaction mixture was stirred for a further 30 minutes then a solution of 1H-indole-6-carboxylic acid methyl ester (10.3 mmol, 1.8 g, 1 equiv.) in dioxane was added portionwise over 5 minutes and the reaction mixture was stirred at 106° C. for 16 hours. The solution was poured onto a 1M aqueous sodium tartrate solution (100 mL) and diluted with dichloromethane (50 mL). The organic layer was separated, dried over Na2SO4 and the solvent was removed under vacuum. The residue was dissolved in dichloromethane (10 mL) and sonicated for 5 minutes. The resultant solid was filtered to afford 1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide, 2.4 g (71% yield). LC @215 nm; Rt 1.50: 97%, m/z (ES+): 330 (M+H+.); δH (250 MHz; d6-DMSO) 10.89 (1H, s), 8.54 (1H, s), 8.32 (2H, m), 8.17 (1H, s), 8.13 (1H, s), 7.70 (2H, m), 7.62 (1H, t), 6.57 (1H, s).

Workup

  1. stirringthe reaction mixture was stirred at 106° C. for 16 hours
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in dichloromethane (10 mL)
  6. customsonicated for 5 minutes
  7. filtrationThe resultant solid was filtered

Sources & evidence

ORD record
ord-72b0f54dd6314ec292f2b2ff30f4c4b9
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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