Sodium borohydride → HCID 67956181, compound

HRID 872279Notes

Reaction equation

HRID 872279 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[C:21]([CH:22]=[O:23])=[CH:20][C:19]([Cl:24])=[CH:18][N:17]=1.[BH4-].[Na+]>CCO>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:13][CH2:14]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[C:21]([CH2:22][OH:23])=[CH:20][C:19]([Cl:24])=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666458HCID 86666458, compound

Product 1

HCID 67956181HCID 67956181, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-5-chloropyridine-3-carbaldehyde (32, 722 mg, 1.77 mmol, 1.0 equiv.) in EtOH (17.7 mL), was added slowly NaBH4 (101 mg, 2.66 mmol, 2.0 equiv.). The reaction mixture was stirred at room temperature until LCMS showed only the desired product. The solvent was evaporated in vacuo. The mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The extracted organic layers were dried over Na2SO4, filtered and concentrated to give the crude product which was purified with normal phase silica gel chromatography (EtOAc/Hexane gradient from 0 to 100%) to obtain product 195 1H NMR (400 MHz, CDCl3): δ 7.89 (s, 2H); 7.57 (d, J=8.8 Hz, 1H); 7.38 (d, J=8.8 Hz, 1H); 4.96 (d, J=5.3 Hz, 2H); 4.52 (d, J=7.1 Hz, 2H); 1.43 (m, 1H); 0.69 (m, 2H); 0.52 (m, 2H). LRMS m/z (M+H) 408.9 and 410.9 found, 408.0 and 410.0 required.

Sources & evidence

ORD record
ord-b4704425aa07421e9bc48cdfa921d549
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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