Dimethylformamide → 9-Benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide

HRID 567221Notes

Reaction equation

HRID 567221 reaction equation
[Na+].[CH2:2]([N:9]1[C:21]2[CH2:20][CH2:19][CH2:18][CH:17]([C:22](=[O:24])[NH2:23])[C:16]=2[C:15]2[C:10]1=[CH:11][C:12]([O:30][CH3:31])=[CH:13][C:14]=2[O:25][CH2:26][C:27]([O-])=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[N:33](C)C=O.[H-].[Na+].BrCC#N>C(OCC)(=O)C.O1CCCC1>[CH2:2]([N:9]1[C:21]2[CH2:20][CH2:19][CH2:18][CH:17]([C:22]([NH2:23])=[O:24])[C:16]=2[C:15]2[C:10]1=[CH:11][C:12]([O:30][CH3:31])=[CH:13][C:14]=2[O:25][CH2:26][C:27]#[N:33])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 23676539[9-Benzyl-4-carbamoyl-7-methoxy-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid sodium salt

Product 1

HCID 101349259-Benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.47 gram (4.19 mmol) of the product from Example 3, Part A in 146 ml. of dimethylformamide and 31 ml. tetrahydrofuran was treated with 210 mg. of sodium hydride (60% in mineral oil; 5.24 mmol) for 10 minutes and then with 0.39 ml. (0.66 mmol) of bromoacetonitrile for 3.5 hours. The mixture was diluted with ethyl acetate, washed with water, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient of 0 to 4% methanol in methylene chloride to give the titled product, 1.34 gram, 82%.

Workup

  1. washwashed with water
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with a gradient of 0 to 4% methanol in methylene chloride

Sources & evidence

ORD record
ord-a105b6b1a2b5493295477dc845a4af17
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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