(Diethylamino)sulfur trifluoride → HCID 73057751, compound

HRID 2207327Notes

Reaction equation

HRID 2207327 reaction equation
O[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:21])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C(N(S(F)(F)[F:28])CC)C>ClCCl>[F:28][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:21])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 73057453HCID 73057453, compound

Product 1

HCID 73057751HCID 73057751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of 3-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-isoquinolin-1-one (55.8 mg, 0.20 mmol) in dichloromethane (0.5 ml) is cooled to −78° C. Diethylaminosulfurtrifluoride (105 μl, 0.80 mmol) is added. The reaction mixture is allowed to reach room temperature within 30 minutes (formation of a clear solution). The reaction mixture is evaporated and the residue is treated with water and saturated sodium hydrogen carbonate solution. The solids are filtered off and chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 3-[4-(1-fluoro-1-methyl-ethyl)-phenyl]-2H-isoquinolin-1-one as fine white powder; HPLC/MS 1.94 min (A), [M+H] 282;

Workup

  1. customThe reaction mixture is evaporated
  2. additionthe residue is treated with water and saturated sodium hydrogen carbonate solution
  3. filtrationThe solids are filtered off
  4. customchromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-1193fcb4dc5a4cb98991ad6b47394915
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

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