(Diethylamino)sulfur trifluoride → HCID 67422345, compound

HRID 1987360Notes

Reaction equation

HRID 1987360 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]2[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:28]O)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(S(F)(F)[F:36])CC)C>C(Cl)Cl>[F:36][CH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][N:9]1[CH:10]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:11][CH2:12][CH2:13][CH:8]1[C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67421095HCID 67421095, compound

Product 1

HCID 67422345HCID 67422345, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of [2-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-phenyl]-methanol (0.107 g,0.28 mmol) in CH2Cl2 (3 mL) was added (diethylamino)sulfur trifluoride (80 μL, 0.61 mmol). After 15 minutes, the cooling bath was removed and the reaction mixture was warmed to room temperature. After an additional 3 hours, the reaction mixture was treated with saturated aqueous NaHCO3 (5 mL) and extracted with CH2Cl2 (4×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.032 g (29%) of COMPOUND 62 as a white solid. 1H NMR (CDCl3) δ 1.60-1.74 (m, 3H), 2.02-2.10 (m, 1H), 2.26-2.41 (m, 8H), 3.56 (s, 2H), 4.13 (d, 2H, J=11.1 Hz), 5.06 (d, 2H, JC-F=48 Hz), 6.81-6.88 (m, 5H), 7.14-7.16 (m, 3H), 8.31 (d, 2H, J=3.6 Hz). 13C NMR (CDCl3) δ 19.24, 25.64, 28.65, 50.09, 67.20, 82.93 (d, JC-F=648 Hz), 122.29, 125.94, 127.47, 127.62, 129.79, 132.36, 133.66 (d, JC-F=62 Hz), 138.14, 139.34, 146.63, 159.99; ES-MS m/z 390 (M+H). Anal. Calcd. For C25H28N3F.0.1H2O: C, 76.73; H, 7.26; N, 10.74. Found: C, 76.66; H, 7.23; N, 10.70.

Workup

  1. customthe cooling bath was removed
  2. waitAfter an additional 3 hours
  3. additionthe reaction mixture was treated with saturated aqueous NaHCO3 (5 mL)
  4. extractionextracted with CH2Cl2 (4×10 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-84ca3a20f7a8457392ef28ae68862711
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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