2,4-Dichlorobenzaldehyde → HCID 11454759, compound

HRID 2115295Notes

Reaction equation

HRID 2115295 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[Cl:11][C:12]1[C:13]([C:29]([F:32])([F:31])[F:30])=[N:14][N:15]([CH2:18][C:19]([N:21]2[CH2:28][CH:27]3[CH:23]([CH2:24][NH:25][CH2:26]3)[CH2:22]2)=[O:20])[C:16]=1[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[Cl:11][C:12]1[C:13]([C:29]([F:32])([F:30])[F:31])=[N:14][N:15]([CH2:18][C:19]([N:21]2[CH2:28][CH:27]3[CH:23]([CH2:24][N:25]([CH2:4][C:3]4[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=4[Cl:1])[CH2:26]3)[CH2:22]2)=[O:20])[C:16]=1[CH3:17]

Participants

7

Reactant 4

HCID 134042,4-DichlorobenzaldehydeHCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 59813964HCID 59813964, compound

Product 1

HCID 11454759HCID 11454759, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,4-dichlorobenzaldehyde (18 mg) and compound 7 (17 mg) in THF (1 mL) was stirred at room temperature for 1 hour and then sodium triacetoxyborohydride (42 mg) was added in one portion. The mixture was stirred at room temperature for another hour and EtOAc (1 mL) was added followed by the addition of saturated aqueous ammonium chloride (1 mL). The aqueous phase was extracted by EtOAc (3×1 mL) and the combined organic extractants was dried, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to afford the title compound 9 as a white solid (15 mg, 80%). LCMS: Rf: 3.605 min, M+H+: 495.

Workup

  1. extractionThe aqueous phase was extracted by EtOAc (3×1 mL)
  2. customthe combined organic extractants was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-bc21b15b46984262a1e6d29c6928bc39
Source dataset
uspto-grants-2008_10
Patent number
US07435831B2

Reaction notes

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