Triethylamine → HCID 69632008, compound

HRID 1358770Notes

Reaction equation

HRID 1358770 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH2:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(N(CC)CC)C.C(=O)=O.CC(C)=O.[O:31](S(C(F)(F)F)(=O)=O)[S:32]([C:35]([F:38])([F:37])[F:36])(=O)=[O:33]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][S:32]([C:35]([F:38])([F:37])[F:36])(=[O:33])=[O:31])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 11424506Ethyl 5-amino-1-methyl-1H-indole-2-carboxylateHCID 18522661Acetone cardice

Product 1

HCID 69632008HCID 69632008, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The N-methyl-5-aminoindole2-carboxylic acid ethyl ester (2.4 g, 11 mmol) was added with 100 ml of CH2Cl2 and triethyl amine (2.3 ml, 16.5 mmol). The reaction mixture was brought to −78 degree (dry ice-acetone) under N2. After (CF3SO2)2O (2.0 ml, 12 mmol) was added into it slowly via a syringe, the reaction mixture was stirred at −78 degree for 30 min and slowly brought to room temperature. The reaction was treated with 300 ml of CH2Cl2 and washed with Sat. Na2SO4 (100 ml×3), H2O (100 ml×50, and brine. TLC (20% EA/Hexane) showed two components, the desired product with smaller Rf value and the corresponding 5-(N,N-ditrifluoromethanesulfonyl)aminoindole. After the solvent was evaporated, the residue was purified either via recrystalization with CH2Cl2/Hexane or Flash Column (20% EA/Hexane). The purified product (1-Methyl-5-trifluoromethansulfonylamino-1H-indole-2-carboxylic acid ethyl ester) was obtained as a light orange solid (1.6 g). 1H-NMR (400 MHz, DMSO-d6) δ 11.69 (s, 1H, SNH-5), 7.64 (d, J=8.6 Hz, 1H, H-7), 7.60 (d, J=2.2 Hz, 1H, H-4), 7.31 (s, 1H, H-3), 7.23 (dd, J=2.2, 8.6 Hz, 1H, H-6), 4.33 (q, J=7 Hz, 2H, CH2CH3), 4.02 (s, 3H, NCH3), 1.33 (t, 3H, CH2CH3), MS m/z 349 [M−H].

Workup

  1. customwas brought to −78 degree
  2. customslowly brought to room temperature
  3. washwashed with Sat. Na2SO4 (100 ml×3), H2O (100 ml×50, and brine
  4. customAfter the solvent was evaporated
  5. customthe residue was purified either via recrystalization with CH2Cl2/Hexane or Flash Column (20% EA/Hexane)

Sources & evidence

ORD record
ord-830a363b45014be4b370374a0f031703
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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