Acetic Acid → HCID 66649423, compound

HRID 469891Notes

Reaction equation

HRID 469891 reaction equation
O([BH-](OC(C)=O)OC(C)=O)C(C)=O.[Na+].[Br:15][C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[N:20][CH:21]=1.[CH:23]1([O:28][C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[CH:32]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1.CC(O)=O>ClCCCl>[Br:15][C:16]1[CH:17]=[C:18]([NH:22][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:29]([O:28][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:30]=2)[CH:19]=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8176813-Amino-5-bromopyridineHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66649423HCID 66649423, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyl-borohydride (245 mg, 1.16 mmol) was added to the solution of 5-bromo-pyridine-3-amine (100 mg, 0.57 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (127 mg, 0.57 mmol) in 10 ml of 1,2-dichloroethtane (DCE), of HOAc (664, 2 eq. 1.16 mmol) was added, the mixture was stirred overnight at room temperature, followed by addition of 15 ml of DCE. The organic phase was washed with water, and dried over sodium sulfate. The solvent was removed by under reduced pressure to give 200 mg of crude 5-bromo-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyridin-3-amine, which was used for the next step without further purification.

Workup

  1. additionwas added
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed by under reduced pressure

Sources & evidence

ORD record
ord-409c85f96c8f4d069245a3ff0e0d4ff3
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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