HCID 57546045, compound → HCID 57546101, compound

HRID 913884Notes

Reaction equation

HRID 913884 reaction equation
[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[CH2:15][CH2:14]3)[N:7]=2)[CH:3]=1.[CH3:16][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([OH:12])[CH3:16])[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 57546045HCID 57546045, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57546101HCID 57546101, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-2-cyclopropyl-2H-indazole-7-carbaldehyde (0.30 g, 1.35 mmol) in tetrahydrofuran (5 mL) at −78° C. was added methyl magnesiumbromide (3 M in diethyl ether, 0.68 mL, 2.03 mmol). The reaction was allowed to gradually warm in the ice bath (ca. 1 h) to 0° C. The reaction which had been a suspension became a solution. The reaction was quenched by addition of saturated ammonium chloride and poured into diethyl ether. The ethereal was washed with water (2×), then brine, dried over sodium sulfate, and concentrated to give 240 mg (77%) as an oil. 1H-NMR (CDCl3, 300 MHz) δ 7.90 (s, 1H), 7.45 (m, 1H), 7.09 (m, 1H), 5.27 (q, J=6.6 Hz, 1H), 3.85-3.93 (m, 1H), 1.65 (d, J=6.6 Hz, 1H), 1.28-1.34 (m, 2H), 1.10-1.17 (m, 2H). Mass spec.: 237.28 (MH)+.

Workup

  1. customThe reaction which
  2. customThe reaction was quenched by addition of saturated ammonium chloride
  3. additionpoured into diethyl ether
  4. washThe ethereal was washed with water (2×)
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give 240 mg (77%) as an oil

Sources & evidence

ORD record
ord-fb12500a18584c6ea67103355e175581
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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