Nitrogen → HCID 44185547, compound

HRID 2387566Notes

Reaction equation

HRID 2387566 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[CH:5]2.[C:16]1([S:22]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:33]([SiH](CC)CC)[CH3:34].FC(F)(F)C(O)=O.N#N.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH2:33][CH3:34])=[O:13])[C:6]([CH3:15])=[C:5]2[CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23]

Participants

8

Reactant 6

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 6409162-(phenylsulfonyl)benzaldehydeHCID 674666192(5-fluoro-2-methyl-1H-indol-1-yl)acetic acid

Product 1

HCID 44185547HCID 44185547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2(5-fluoro-2-methyl-1H-indol-1-yl)acetic acid (1.29 g, 1.49 mmol), 2-(phenylsulfonyl)benzaldehyde (1.50 g, 6.10 mmol) and triethylsilane (4.30 ml, 27.0 mmol) in dichloromethane (40 ml) was added trifluoroacetic acid (1.25 ml, 16.5 mmol) dropwise under N2 at 0° C. over 30 minutes. The reaction was warmed to room temperature and stirred for 2 hours. Saturated aqueous sodium hydrogen carbonate solution was added and the product extracted with dichloromethane. The combined organic extracts were washed with saturated brine, dried over MgSO4 and concentrated in vacuo giving a brown oil which was triturated with petroleum ether (40-60° C.) to give a white solid (1.34 g, 2.88 mmol 52%).

Workup

  1. extractionthe product extracted with dichloromethane
  2. washThe combined organic extracts were washed with saturated brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customgiving a brown oil which
  6. customwas triturated with petroleum ether (40-60° C.)
  7. customto give a white solid (1.34 g, 2.88 mmol 52%)

Sources & evidence

ORD record
ord-96feebdf09ae4bd08e7c4f53e5e68ac0
Source dataset
uspto-grants-2012_09
Patent number
US08268878B2

Reaction notes

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