Sodium borohydride → N-(1-benzyl-1H-indazol-4-yl)-7-(1-hydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706738Notes

Reaction equation

HRID 706738 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]2[C:10]([C:13]([NH:15][C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[N:19][N:20]4[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:14])=[CH:11][N:12]=[C:6]2[CH:5]=1)(=[O:3])[CH3:2].C1COCC1.CO.[BH4-].[Na+]>CO.C(Cl)Cl>[CH2:25]([N:20]1[C:21]2[C:17](=[C:16]([NH:15][C:13]([C:10]3[N:7]4[CH:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][C:6]4=[N:12][CH:11]=3)=[O:14])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[N:19]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21899815MeOH tetrahydrofuranHCID 679759587-acetyl-N-(1-benzyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 86699349N-(1-benzyl-1H-indazol-4-yl)-7-(1-hydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamideYield 89.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 7-acetyl-N-(1-benzyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (Example 146; 10 mg, 0.024 mmol) in a 1:1 THF/MeOH mixture (0.2 mL) was treated at ambient temperature with excess sodium borohydride (3.7 mL, 0.10 mmol), and stirring continued overnight. The reaction was quenched with excess saturated aqueous sodium bicarbonate and the resulting suspension was extracted with EtOAc and DCM. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with MeOH/DCM as eluent to afford 8.8 mg of the desired product as a white solid. MS (ES+APCI) m/z=412 (M+H) detected.

Workup

  1. customThe reaction was quenched with excess saturated aqueous sodium bicarbonate
  2. extractionthe resulting suspension was extracted with EtOAc and DCM
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto afford the crude product

Sources & evidence

ORD record
ord-7646dfa14ab94bbe9e41dc8205f60ccd
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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