2-Fluoro-6-methoxybenzaldehyde → 5-(3-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1H-pyrazol-1-yl)-3-(pyridin-4-yl)-1H-indazole

HRID 1465713Notes

Reaction equation

HRID 1465713 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[CH:20]=[CH:19][C:18]([CH:21]5[CH2:26][CH2:25][CH2:24][N:23]([C:27](OC(C)(C)C)=O)[CH2:22]5)=[N:17]4)[CH:14]=3)[NH:9][N:8]=2)=[CH:3][CH:2]=1.[F:34][C:35]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[C:36]=1C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[F:34][C:35]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[C:36]=1[CH2:27][N:23]1[CH2:24][CH2:25][CH2:26][CH:21]([C:18]2[CH:19]=[CH:20][N:16]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[NH:9][N:8]=[C:7]4[C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[N:17]=2)[CH2:22]1

Participants

5

Reactant 3

HCID 27373572-Fluoro-6-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67517259tert-butyl 3-(1-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate

Product 1

HCID 569694475-(3-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1H-pyrazol-1-yl)-3-(pyridin-4-yl)-1H-indazoleYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 3-(1-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate (30 mg, 0.09 mmol) in THF (2 mL) were added 2-fluoro-6-methoxybenzaldehyde (20 mg, 0.13 mmol) and sodium triacetoxyborohydride (30 mg, 0.14 mmol). After 3 h, the reaction mixture was quenched with saturated NaHCO3 and extracted with EtOAc. After concentration, crude mixture was column purified with mixture of methanol, dichloromethane and ammonia to give 5-(3-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1H-pyrazol-1-yl)-3-(pyridin-4-yl)-1H-indazole (37 mg).

Workup

  1. customthe reaction mixture was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. concentrationAfter concentration, crude mixture
  4. custompurified with mixture of methanol, dichloromethane and ammonia

Sources & evidence

ORD record
ord-cf8a4cd0c29e44369e7be8a8c5574964
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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