Water → HCID 86705065, compound

HRID 1477938Notes

Reaction equation

HRID 1477938 reaction equation
O.[F-].[K+].[Si]([C:8]([F:11])([F:10])[F:9])(C)(C)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:24]2[C:32]3[C:27](=[C:28]([N:33]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25]2)([CH2:22][CH3:23])[C:20]#[CH:21])=[CH:15][CH:14]=1>CN(C=O)C.[Cu]I>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:24]2[C:32]3[C:27](=[C:28]([N:33]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25]2)([C:22]#[C:23][C:8]([F:11])([F:10])[F:9])[CH2:20][CH3:21])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86705050HCID 86705050, compound

Product 1

HCID 86705065HCID 86705065, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent2×

Procedure

A three-neck round-bottom flask was charged with CuI (38 mg, 0.2 mmol), Phen.H2O (40 mg, 0.2 mmol), KF (58 mg, 1.0 mmol) and stirring bar. The flask was dried at 130° C. in vacuo for 3 h. After cooling to RT, the flask was backfilled with air and TMSCF3 (142 mg, 1.0 mmol), DMF (2 mL) was added. Then the flask was heated to 130° C. for 30 min. A solution of N-(1-(3-(4-chlorophenyl)pent-1-yn-3-yl)-1H-indol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide (102 mg, 0.2 mmol, enantiomer A) in DMF (1 mL) was slowly added to the mixture at 130° C. over 1 h. The resulting mixture was stirred for another 1 h at 130° C. The crude product was purified by Combiflash (mobile phase: CH3CN/water (0.08% of NH4HCO3)) to give the title compound. LC/MS m/z=606.7 [M+Na]

Workup

  1. customThe flask was dried at 130° C. in vacuo for 3 h
  2. additionwas added
  3. temperatureThen the flask was heated to 130° C. for 30 min
  4. customThe crude product was purified by Combiflash (mobile phase: CH3CN/water (0.08% of NH4HCO3))

Sources & evidence

ORD record
ord-436fb82fe9e94709a147c20e15cf0f18
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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