Triethylamine → HCID 57546045, compound

HRID 913883Notes

Reaction equation

HRID 913883 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[C:8]2[C:4](=[CH:5][N:6]([CH:13]3[CH2:15][CH2:14]3)[N:7]=2)[CH:3]=1.C(N(CC)CC)C>CS(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[C:8]2[C:4](=[CH:5][N:6]([CH:13]3[CH2:14][CH2:15]3)[N:7]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 57545966HCID 57545966, compound

Product 1

HCID 57546045HCID 57546045, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
0 °C

Procedure

(5-Chloro-2-cyclopropyl-2H-indazol-7-yl)methanol (0.39 g, 1.75 mmol) and triethylamine (0.73 mL, 5.25 mmol) were combined in dimethyl sulfoxide (4 mL) and cooled to 0° C. The reaction was treated with sulfur trioxide pyridine complex (0.87 g, 5.25 mmol) in dimethyl sulfoxide (2 mL), stirred at 0° C. for 5 min, and at room temperature for 20 min. The reaction was poured into ice water and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with 10% acetic acid (2×), water (2×), saturated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) gave 298 mg (77%) as a yellow solid. 1H-NMR (CDCl3, 300 MHz) δ 10.52 (s, 1H), 8.05 (s, 1H), 7.84 (d, J=2.2 Hz, 1H), 7.77 (d, J=1.8 Hz, 1H), 3.96-4.03 (m, 1H), 1.35-1.40 (m, 2H), 1.16-1.23 (m, 2H). Mass spec.: 221.30 (MH)+.

Workup

  1. waitat room temperature for 20 min
  2. extractionextracted with ethyl acetate (2×)
  3. washwashed with 10% acetic acid (2×), water (2×), saturated sodium bicarbonate (2×), brine (2×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography on silica gel (30% ethyl acetate/hexanes) gave 298 mg (77%) as a yellow solid

Sources & evidence

ORD record
ord-3dbd26e6ed4a4382bd86b0f536ca240e
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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