Lithiumtriethylborohydride → HCID 71621911, compound

HRID 1473895Notes

Reaction equation

HRID 1473895 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[O:20])[O:12]3)[C:5]=12.C([BH-](CC)CC)C.[Li+]>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]([OH:20])[O:12]3)[C:5]=12

Participants

4

Reactant 2

HCID 23664628LithiumtriethylborohydrideHCID 86690719HCID 86690719, compound

Product 1

HCID 71621911HCID 71621911, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-(imidazo[1,2-a]pyridin-8-ylmethyl)isobenzofuran-1(3H)-one (80 mg, 0.3 mmol) in DCM (6 mL) at −78° C., was added lithium triethyl borohydride (1M/THF, 0.3 mL) dropwise. The reaction mixture was stirred at −78° C. for 30 min, diluted with DCM (\; 10 mL), and quenched with MeOH (1 mL) and 5% HCl (2 mL). The mixture was warmed up to rt and stirred for 1 h. The solvents were removed and the residue was purified on RP-HPLC using CH3CN and water as eluent to give 3-(imidazo[1,2-a]pyridin-8-ylmethyl)-1,3-dihydroisobenzofuran-1-ol (20 mg, 25%). 1H NMR (400 MHz, CD3OD) δ=8.56 (t, 1H), 8.97 (d, 1H), 7.74 (s, 1H), 7.45-7.32 (m, 5H), 7.07-7.00 (m, 1H), 6.38-6.30 (m, 1H), 5.84-5.80 (m, 0.5H), 5.56 (dd, 0.5H), 3.69 (t, 0.5H), 3.65 (t, 0.5H), 3.26 (dd, 0.5H), 3.13 (dd, 0.5H). LRMS (M+H+) m/z 267.1.

Workup

  1. customquenched with MeOH (1 mL) and 5% HCl (2 mL)
  2. temperatureThe mixture was warmed up to rt
  3. stirringstirred for 1 h
  4. customThe solvents were removed
  5. customthe residue was purified on RP-HPLC

Sources & evidence

ORD record
ord-43d592003ac041f7820ded36a57ef3df
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

Loading…