Dicyclohexylcarbodiimide → t-Butyl 5-{[5-(2-pyridyldithiomethyl)benzofuran-2-ylcarbonyl]amino}indole-2-carboxylate

HRID 2259845Notes

Reaction equation

HRID 2259845 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([OH:20])=O)=[CH:15][C:14]=2[CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:41]2>C1COCC1.C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([NH:37][C:38]3[CH:39]=[C:40]4[C:44](=[CH:45][CH:46]=3)[NH:43][C:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:41]4)=[O:20])=[CH:15][C:14]=2[CH:21]=1

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10633339Tert-butyl 5-amino-1H-indole-2-carboxylateHCID 153454855-(2-Pyridyldithiomethyl)benzofuran-2-carboxylic acid

Product 1

HCID 15345486t-Butyl 5-{[5-(2-pyridyldithiomethyl)benzofuran-2-ylcarbonyl]amino}indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 15 (247 mg, 0.78 mmol) in 30 mL dry THF at room temperature under argon, was treated sequentially with solutions of dicyclohexylcarbodiimide (177 mg, 0.86 mmol) in 5 mL methylene chloride, 4-(dimethylamino)pyridine (29 mg, 0.23 mmol) in 2 mL methylene chloride, and 10 (200 mg, 0.86 mmol) in 5 mL methylene chloride. The reaction mixture was stirred overnight. Dicyclohexylurea was filtered from the reaction mixture, and the filtrate was washed with water, cold 0.1M HCl, saturated aqueous sodium bicarbonate, and water. The organic solution was dried over magnesium sulfate, filtered, and concentrated to give a dark oil. The crude product was further purified by chromatography on a silica gel column, eluting with ethyl acetate:hexanes to give 16 as an off-white solid: NMR (acetone-d6) δ 1.6 (s, 9H), δ 4.3 (s, 2H), δ 7.0-8.6 (m, 12H).

Workup

  1. filtrationDicyclohexylurea was filtered from the reaction mixture
  2. washthe filtrate was washed with water, cold 0.1M HCl, saturated aqueous sodium bicarbonate, and water
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark oil
  7. customThe crude product was further purified by chromatography on a silica gel column
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1a9d81e659c84128a86f8f2a65390cfd
Source dataset
uspto-grants-1995_12
Patent number
US05475092

Reaction notes

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