Benzoyl chloride → HCID 57457114, compound

HRID 1361031Notes

Reaction equation

HRID 1361031 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].C(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:19]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 27513Indole-5-carbonitrile

Product 1

HCID 57457114HCID 57457114, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-cyanoindole (1.0 g, 7.0 mmol) in dichloromethane (8 mL) was added 4-(dimethylamino)pyridine (0.171 g, 1.4 mmol), triethylamine (1.96 mL, 1.42 g, 14 mmol) and benzoyl chloride (0.89 mL, 1.08 g, 7.7 mmol). The resulting mixture was stirred for 18 hours at room temperature. The mixture was diluted with dichloromethane (80 mL) and washed consecutively with a saturated solution of sodium hydrogencarbonate (40 mL) and brine (40 mL). The organic phase was dried with magnesium sulfate (1 hour). Filtration and concentration furnished the crude material which was purified by flash chromatography on silica gel, eluting with ethyl acetate/heptanes=2:3. 1-Benzoyl-1H-indole-5-carbonitrile was obtained as a solid.

Workup

  1. washwashed consecutively with a saturated solution of sodium hydrogencarbonate (40 mL) and brine (40 mL)
  2. dry with materialThe organic phase was dried with magnesium sulfate (1 hour)
  3. filtrationFiltration and concentration
  4. customfurnished the crude material which
  5. customwas purified by flash chromatography on silica gel
  6. washeluting with ethyl acetate/heptanes=2:3

Sources & evidence

ORD record
ord-911170f702274ede9b1b463d147c53bf
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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