(Diethylamino)sulfur trifluoride → HCID 18412755, compound

HRID 992488Notes

Reaction equation

HRID 992488 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[C:6]([C:8]2(O)[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:21])[CH:7]=1.C(N(S(F)(F)[F:41])CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[C:6]([C:8]2([F:41])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:21])[CH:7]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 18412756HCID 18412756, compound

Product 1

HCID 18412755HCID 18412755, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (±)-3-[5-chloro-2-[4-(trifluoromethyl)phenyl-methoxy]phenyl]-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indole-2-one (Preparation 6, 45 mg, 0.09 mmol) in CH2Cl2 (3 mL), was added dropwise neat diethylaminosulfur trifluoride (0.018 mL, 0.135 mmol) at −78° C. The reaction mixture was warmed to room temperature for 15 minutes and then quenched with water. The organic layer was separated, washed with water, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to provide the title compound (35 mg, 77% yield). MS m/e 502 (MH−). 1H NMR (CDCl3): δ7.84 (d, J=1.95 Hz, 1H), 7.68 (s, 1H), 7.53 (d, J=8.1 Hz, 2H), 7.36 (dd, J=8.7 Hz, 2.5 Hz, 1H), 7.29 (m, 1H), 7.21 (m, 1H), 7.05 (d, J=8.1 Hz, 2H), 6.81(dd, J=8.8 Hz, 1.1 Hz, 1H), 6.73 (s, 1H), 4,88 (d, 11.0 Hz, 1H), 4.73 (d, J=11.0 Hz,1H).

Workup

  1. customquenched with water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-875a74825cf948049d2c910f2a030822
Source dataset
uspto-grants-2002_10
Patent number
US06469042B1

Reaction notes

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