Indole-5-carboxaldehyde → HCID 86603028, compound

HRID 735465Notes

Reaction equation

HRID 735465 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=2)=[C:12]2[C:7]([C:8]([C:21]([F:24])([F:23])[F:22])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.[NH:31]1[C:39]2[C:34](=[CH:35][C:36]([CH:40]=O)=[CH:37][CH:38]=2)[CH:33]=[CH:32]1.C([O-])=O.[Na+].C([BH3-])#N.[Na+]>CO>[NH:31]1[C:39]2[C:34](=[CH:35][C:36]([CH2:40][NH:20][C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([C:13]4[N:5]([CH2:4][C:3]5[C:2]([F:1])=[CH:28][C:27]([F:29])=[CH:26][C:25]=5[F:30])[N:6]=[C:7]5[C:12]=4[CH:11]=[CH:10][CH:9]=[C:8]5[C:21]([F:22])([F:23])[F:24])[CH:15]=3)=[CH:37][CH:38]=2)[CH:33]=[CH:32]1

Participants

6

Reactant 4

HCID 589040Indole-5-carboxaldehydeHCID 2723810Sodium FormateHCID 5003444Sodium cyanoborohydrideHCID 86603024HCID 86603024, compound

Product 1

HCID 86603028HCID 86603028, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}amine (0.1 g, 0.24 mmol), indole 5-carboxaldehyde (0.035 g, 0.24 mmol), sodium formate (0.189 g, 3 mmol) and sodium cyanoborohydride (0.188 g, 3 mmol) in methanol (3 mL) was heated at 60° C. overnight. The reaction mixture was cooled, and concentrated in vacuo. The residue was partitioned with ethyl acetate and ammonium hydroxide. The organic phase was concentrated in vacuo to afford crude product, which was purified by flash chromatography (silic gel 60, methylene chloride) to afford the title compound (0.031 g, 24%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned with ethyl acetate and ammonium hydroxide
  4. concentrationThe organic phase was concentrated in vacuo
  5. customto afford crude product, which
  6. customwas purified by flash chromatography (silic gel 60, methylene chloride)

Sources & evidence

ORD record
ord-0ab21fd63e5d4b27a1e0baaf46b63e7b
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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