Acetic Acid → HCID 59401395, compound

HRID 2060888Notes

Reaction equation

HRID 2060888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH:21]=O)=[CH:13][CH:12]=1)[C:5]#[N:6].C(O)(=O)C.[CH3:27][CH:28]([CH3:32])[CH2:29][CH2:30][NH2:31].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][NH:31][CH2:30][CH2:29][CH:28]([CH3:32])[CH3:27])=[CH:13][CH:12]=1)[C:5]#[N:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7894IsoamylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59401365HCID 59401365, compound

Product 1

HCID 59401395HCID 59401395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-4-(4-formylnaphthalen-1-yloxy)benzonitrile (Preparation 82) (800 mg, 2.60 mmol) in DCM (35 mL) was added acetic acid (0.7 mL, 7.80 mmol), 3-methylbutylamine (0.91 mL, 7.80 mmol) and NaBH(OAc)3 (1.65 g, 7.80 mmol). The reaction was stirred at rt for 16 h. The mixture was partitioned between DCM (150 mL) and saturated NaHCO3 (200 mL) and the organic phase dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (EtOAc:isohexane 1:1) to give the title compound: RT=3.01 min; m/z (ES+)=379.3, 381.2 [M+H]+.

Workup

  1. customThe mixture was partitioned between DCM (150 mL) and saturated NaHCO3 (200 mL)
  2. dry with materialthe organic phase dried (MgSO4)
  3. customSolvent was removed in vacuo
  4. customthe residue purified by column chromatography (EtOAc:isohexane 1:1)

Sources & evidence

ORD record
ord-4373401120374b228797e2a289345ad2
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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