Sodium triacetoxyborohydride → HCID 178515500, compound

HRID 1013846Notes

Reaction equation

HRID 1013846 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH:7]([CH2:13][CH:14]=O)[C:8]([O:10]CC)=O)=[C:4]([Cl:18])[CH:3]=1.Cl.[NH:20]1[C:28]2[CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24][C:23]=2[CH:22]=[N:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH:7]2[CH2:13][CH2:14][N:29]([CH:26]3[CH2:27][C:28]4[C:23](=[CH:22][NH:21][N:20]=4)[CH2:24][CH2:25]3)[C:8]2=[O:10])=[C:4]([Cl:18])[CH:3]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 673173104,5,6,7-Tetrahydro-2H-indazol-6-amine hydrochlorideHCID 86629116Ethyl 2-(4-bromo-2-chlorobenzyl)-4-oxobutanoate

Product 1

HCID 178515500HCID 178515500, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Combine ethyl 2-(4-bromo-2-chlorobenzyl)-4-oxobutanoate (0.92 g, 2.8 mmol), 4,5,6,7-tetrahydro-1H-indazol-6-amine hydrochloride (preparation 80) (490 mg, 2.8 mmol) and sodium triacetoxyborohydride (886 mg, 4.2 mmol) in dichloroethane (50 mL) and stir for 48 hours at room temperature. Add water and extract with CH2Cl2. Dry the organic layer over magnesium sulfate, filter and concentrate. Purify the residue by silica gel chromatography affords the title compound (428 mg, 68%): MS (m/z): 410 (M+2).

Workup

  1. extractionAdd water and extract with CH2Cl2
  2. dry with materialDry the organic layer over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography

Sources & evidence

ORD record
ord-e75f9f11803d467386e428898e6c6b6c
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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