Water → HCID 57901911, compound

HRID 1928555Notes

Reaction equation

HRID 1928555 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][NH:8]1.[F:17][C:18]([F:33])([F:32])[S:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+]([O-])=O)=[CH:25][CH:24]=1)(=[O:21])=[O:20].O>CN(C=O)C>[F:17][C:18]([F:33])([F:32])[S:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]2[C:25](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:24]=1[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][NH:8]1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 5498704-Nitrophenyl trifluoromethanesulfonate

Product 1

HCID 57901911HCID 57901911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Powdered K2CO3 (2.30 g, 17 mmol) was added to a solution of 1 (2.30 g, 8.4 mmol) and 4-nitrophenyl trifluoromethanesulfonate (2.28 g, 8.4 mmol) in DMF (70 mL). After 3 hours, the mixture was poured into water (300 mL) and extracted with CH2Cl2 (250 mL, 3 times). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to provide crude 2 as an oil which was purified by column chromatography on silica gel (5:1 hexanes/EtOAc). The fractions containing the product (Rf=0.50, 5:1 hexanes/EtOAc) were collected and concentrated under reduced pressure to yield the title product 2 (3.15 g, 92% yield) as an oil. 1H NMR (CDCl3, 400 MHz, ppm): δ 8.18 (d, J=8.8 Hz, 1H), 7.92-7.83 (m, 2H), 7.46-7.11 (m, 5H), 6.92 (t, J=7.2 Hz, 1H), 6.51 (d, J=7.6 Hz, 1H), 5.97 (s, 1H), 3.54-3.28 (m, 3H), 2.94 (d, J=14.8, 1H), 2.31 (s, 1H); 13C NMR (CDCl3, 75 MHz, ppm): δ 146.03, 137.81, 134.57, 133.68, 131.97, 131.48, 131.02, 129.22, 128.45, 128.07, 126.71, 126.59, 126.32, 126.11, 120.75, 118.98, 116.51, 55.86, 44.96, 29.67.

Workup

  1. extractionextracted with CH2Cl2 (250 mL, 3 times)
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d73aeb0d32d4f278dcd6da6e9842ab6
Source dataset
uspto-grants-2012_05
Patent number
US08183378B2

Reaction notes

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