1,2-Dichloroethane → 1H-Indole-2-carboxamide

HRID 1420458Notes

Reaction equation

HRID 1420458 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C1C=CC2N(O)N=[N:19]C=2C=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:19])=[O:12]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 72899Indole-2-carboxylic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 5948321H-Indole-2-carboxamideYield 236.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To intermediate 34 G (102.9 mg, 0.24 mmol) in DCM (5 mL) was added 2-indole carboxylic acid (47 mg, 0.29 mmol), HOBT (39 mg, 0.29 mmol), EDC (56 mg, 0.29 mmol) and 2d triethylamine. The reaction mixture was stirred for 16 h, diluted with EtOAc (100 mL), washed with saturated NaHCO3 (2×20 mL), 1N aqueous HCl (2×20 mL), brine (1×20 mL), dried (MgSO4), and concentrated to give the indole amide (110 mg, 80%). Rf =0.58 (10% methanol/DCM); 1HNMR (300 MHz, CDCl3) d 1.04 (d, J=6.8 Hz, 3H), 1.06 (d, J=6.8 Hz, 3H), 1,39 (s, 6H), 3.58 (d, J=16.6 Hz, 1H), 3.83 (s, 3H), 4.59 (d, J=16.6 Hz, 1H), 4.76 (d, J=8.5 Hz, 1H), 5.03 (m, 1H), 6.89 (m, 2H), 6.98 (m, 3H), 7.13 (m, 2H), 7.45 (m, 3H), 7.61 (m, 2H), 8.98 (s, 1H); MS(FAB) m/z 571.2 (MH+).

Workup

  1. washwashed with saturated NaHCO3 (2×20 mL), 1N aqueous HCl (2×20 mL), brine (1×20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-abb27a80f92b45bf9181d414fb7bfd4a
Source dataset
uspto-grants-1999_03
Patent number
US05889182

Reaction notes

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