Sodium borohydride → HCID 59024395, compound

HRID 1678218Notes

Reaction equation

HRID 1678218 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[CH:18]=[O:19])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]1=2.[BH4-].[Na+]>CO>[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([C:15]3[CH:16]=[C:17]([CH2:18][OH:19])[CH:20]=[CH:21][CH:22]=3)[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59024185HCID 59024185, compound

Product 1

HCID 59024395HCID 59024395, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-benzaldehyde (Preparation #25, F (using 3-bromobenzaldehyde), 50 mg, 0.14 mmol), and NaBH4 (0.01 g, 0.26 mmol) in MeOH (2 mL) was stirred at ambient temperature for about 1 hour. The reaction mixture was concentrated under reduced pressure then the residue was purified by reverse phase preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min; 5-50% CH3CN/50 mM aqueous ammonium acetate over 20 min; 50-100% CH3CN/50 mM aqueous ammonium acetate over 1 min; hold at 100% CH3CN for 5 minutes, 21 mL/min) to yield [3-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-phenyl]-methanol (6 mg, 12%); (DMSO-d6, 400 MHz) 8.8 (d, 1H), 8.55 (d, 1H), 8.37 (s, 1H), 8.19 (d, 1H), 8.18 (s, 1H), 8.10 (t, 1H), 8.04 (dd, 1H), 7.93 (dd, 1H), 7.89 (d, 1H, 7.45 (m, 2H), 5.40 (t, 1H), 4.6 (d, 2H); RP-HPLC (Table 1, Method e) Rt=1.85 min; m/z: (M−H)− 355.8.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min; 5-50% CH3CN/50 mM aqueous ammonium acetate over 20 min; 50-100% CH3CN/50 mM aqueous ammonium acetate over 1 min; hold at 100% CH3CN for 5 minutes, 21 mL/min)

Sources & evidence

ORD record
ord-5626f7c4de1b4819a6ff709f965a3dcc
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

Loading…