Sodium borohydride → HCID 90095814, compound

HRID 2284610Notes

Reaction equation

HRID 2284610 reaction equation
[BH4-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:4]=1[C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[CH2:19][CH2:18]2>CO>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[C:4]=1[C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH:20]([OH:24])[CH2:19][CH2:18]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86715526HCID 86715526, compound

Product 1

HCID 90095814HCID 90095814, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (21 mg) was added to a stirring solution of 5-([3,4′-bipyridin]-2-yl)-2,3-dihydro-1H-inden-1-one (162 mg) in MeOH (4 mL). The reaction mixture was concentrated and quenched with aq. NH4Cl. The resultant solid was extracted into CH2Cl2 (2×20 mL). Combined organic layers were stirred over MgSO4, filtered and concentrated. Flash chromatographic purification (Combiflash® companion System® with RediSep® silica gel column 12 g, 50-75% EtOAc/hexanes as eluting solvent) provided rac-5-([3,4′-bipyridin]-2-yl)-2,3-dihydro-1H-inden-1-ol (170 mg) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 8.69 (dd, J=4.8, 1.6 Hz, 1H), 8.48 (d, J=6.0 Hz, 2H), 7.85 (dd, J=7.8, 1.7 Hz, 1H), 7.48 (dd, J=7.8, 4.7 Hz, 1H), 7.25-7.11 (m, 4H), 7.00 (dd, J=7.8, 1.5 Hz, 1H), 5.29-5.20 (m, 1H), 5.00 (q, J=6.4 Hz, 1H), 2.81 (ddd, J=16.0, 8.7, 3.9 Hz, 1H), 2.61 (dt, J=15.9, 8.0 Hz, 1H), 2.36-2.21 (m, 1H), 1.74 (dtd, J=12.8, 8.2, 6.3 Hz, 1H). LCMS: rt 2.81 min (A), purity 99%, MS (m/e) 289 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customquenched with aq. NH4Cl
  3. extractionThe resultant solid was extracted into CH2Cl2 (2×20 mL)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customFlash chromatographic purification (Combiflash® companion System® with RediSep® silica gel column 12 g, 50-75% EtOAc/hexanes as eluting solvent)

Sources & evidence

ORD record
ord-5fb6a4b4e4114befb324dc6a46172676
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

Loading…