Acetonitrile → (S)-1-(1-(4-Methoxybenzyl)-1H-indazol-6-yl)ethane-1,2-diol

HRID 1410339Notes

Reaction equation

HRID 1410339 reaction equation
C[C:2]([OH:5])([CH3:4])[CH3:3].C(#N)C.[CH3:9][O:10][C:11]1[CH:28]=[CH:27][C:14]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][CH:21]=C(C=C)[CH:23]=3)[CH:18]=[N:17]2)=[CH:13][CH:12]=1.CCCCCC.CC[O:37]CC>O>[CH3:9][O:10][C:11]1[CH:28]=[CH:27][C:14]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:3]([C@H:2]([OH:5])[CH2:4][OH:37])[CH:23]=3)[CH:18]=[N:17]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6386tert-ButanolHCID 21584099Diethylether hexaneHCID 682292411-(4-Methoxybenzyl)-6-vinyl-1H-indazole

Product 1

HCID 67459202(S)-1-(1-(4-Methoxybenzyl)-1H-indazol-6-yl)ethane-1,2-diolYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of tBuOH (10 mL), H2O (10 mL), ACN (1.8 mL) and ADmix-α (1.28 g) was stirred for 5 min at room temperature and then cooled to 0° C. at which time 1-(4-methoxybenzyl)-6-vinyl-1H-indazole (320 mg, 1.21 mmol) was added. The reaction was stirred for 18 h and allowed to warm to room temperature. The reaction was then diluted with H2O (25 mL) and extracted 3× with CH2Cl2. The organic layer was separated, washed with brine, dried over MgSO4 and the solvent removed to give a white solid which was sonicated with hexane/Et2O (1:1) and then filtered to give the title compound (270 mg, 75% after drying); 1H NMR (400 MHz, CD3OD) δ 8.01 (s, 1H), 7.72 (d, J=8.2 Hz, 1H), 7.58 (s, 1H), 7.19-7.13 (m, 3H), 6.82 (d, J=8.4 Hz, 2H), 5.56 (s, 2H), 4.82-4.79 (m, 1H), 3.73 (s, 3H), 3.69-3.59 (m, 2H); MS ESI 298.9 [M+H]+, calcd for [C17H18N2O3+H]+ 299.14.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred for 18 h
  3. temperatureto warm to room temperature
  4. extractionextracted 3× with CH2Cl2
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed
  9. customto give a white solid which
  10. filtrationfiltered

Sources & evidence

ORD record
ord-7725c340556c48e78b6bc58e77a63d38
Source dataset
uspto-grants-2014_12
Patent number
US08921545B2

Reaction notes

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