1,2-Dichloroethane → HCID 69631947, compound

HRID 1358771Notes

Reaction equation

HRID 1358771 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:19]([OH:21])=O.[CH:22]1[CH:23]=[CH:24][C:25]2N(O)N=[N:28][C:26]=2[CH:27]=1.C(Cl)CCl.NC1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[C:26]1([NH:28][C:19]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][C:7]([NH:11][S:12]([C:15]([F:16])([F:18])[F:17])(=[O:14])=[O:13])=[CH:8][CH:9]=3)=[O:21])[CH:27]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 18185336HCID 18185336, compound

Product 1

HCID 69631947HCID 69631947, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 1-Methyl-5-Trifluoromethansulfonylamino-1H-Indole-2-Carboxylic Acid (0.21 g, 0.65 mmol) in 8 ml of DMF was added HOBt (96 mg, 0.71 mmol), EDC (145 mg, 0.78 mmol), TEA (131 mg, 1.3 mmol), and aniline (0.65 ml, 72 mmol). The reaction mixture was stirred at room temperature for a day. The reaction was diluted with 200 ml of methylene dichloride and washed with water and brine, then concentrated. The residue was purified by flash column with 50% EtOAc/Hexane to give 0.13 g of 1-Methyl-5-trifluoromethansulfonylamino-1H-indole-2-carboxylic acid phenylamide as a beige solid. 1H-NMR (400 MHz, DMSO-d6) δ 11.61 (s, 1H, SNH), 10.37 (s, 1H, NHCO), 7.78 (d, J=8 Hz, 2H, ArH-o), 7.63 (d, J=9 Hz, 1H, H-7), 7,61 (d, J=2 Hz, 1H, H-4), 7.37 (t, J=8 Hz, 2H, ArH-m), 7.32 (s, 1H, H-3), 7.20 (dd, J=2, 9 Hz, 1H, H-6), 7.12 (t. J=7.4 Hz, 1H. ArH-p).MS m/z 396 (M−H).

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated
  3. customThe residue was purified by flash column with 50% EtOAc/Hexane

Sources & evidence

ORD record
ord-a6a4a13468f14130a69fc5d7e3925c6d
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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