Isoamylamine → HCID 57937835, compound

HRID 1435059Notes

Reaction equation

HRID 1435059 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[CH2:12]([NH2:17])[CH2:13][CH:14]([CH3:16])[CH3:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[K+]>ClC(Cl)C>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6][NH:17][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 4

HCID 7894IsoamylamineHCID 14797Potassium HydroxideHCID 27732904-Bromo-2,6-difluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57937835HCID 57937835, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-Bromo-2,6-difluoro-benzaldehyde (I-1a: 30 g) and isoamyl amine (13 g) were combined in dichloroethane (1 L) at ambient temperature. After stirring for 2 hours, sodium triacetoxyborohydride (144 g) was added to the reaction mixture. After stirring overnight, the reaction mixture was treated with a 2 M aqueous potassium hydroxide solution. The layers were separated and the organic phase dried over magnesium sulfate before being filtered and concentrated with a rotary evaporator to provide the title compound (I-1b) as an oil, which was used in the subsequent transformation without further purification.

Workup

  1. stirringAfter stirring overnight
  2. customThe layers were separated
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. filtrationbefore being filtered
  5. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-9a8360b127c244119525959f273ff1a5
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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