Water → HCID 59463859, compound

HRID 1645179Notes

Reaction equation

HRID 1645179 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([NH2:17])=O)[CH:13]=2)[C:8]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[CH:7]1.CCN(CC)CC.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:17])[CH:13]=2)[C:8]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[CH:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 59463837HCID 59463837, compound

Product 1

HCID 59463859HCID 59463859, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) suspension of 1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indole-6-carboxylic acid amide (15 mg, 0.034 mmol) and Et3N (10 μL, 0.072 mmol) in CH2Cl2 (1.5 mL) was added Tf2O (13 μL, 0.077 mmol). The mixture was stirred at 0° C. for 2 h and then at room temperature for 20 h. Water (25 mL) was added and the mixture was extracted with CH2Cl2 (2×25 mL). The combined organic phases were dried (Na2SO4) and concentrated to give the title compound as a yellow solid (13 mg, yield: 91%).

Workup

  1. temperatureTo a cooled
  2. waitat room temperature for 20 h
  3. extractionthe mixture was extracted with CH2Cl2 (2×25 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-989ca878f77640949144443c13b36edb
Source dataset
uspto-grants-2012_02
Patent number
US08124647B2

Reaction notes

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