Acetic Acid → HCID 43283713, compound

HRID 1454228Notes

Reaction equation

HRID 1454228 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:3]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:20][CH:17]2[CH2:19][CH2:18]2)=[C:4]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 43364728HCID 43364728, compound

Product 1

HCID 43283713HCID 43283713, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-bromo-2-(pyridin-3-yloxy)-benzaldehyde (2.0 g, 7.19 mmol) in DCE (75 mL) were added cyclopropylamine (0.50 mL, 7.2 mmol), acetic acid (2.16 mL, 36.0 mmol), and NaBH(OAc)3 (95%; 3.62 g, 18.0 mmol) portionwise. After 18 h, the mixture was diluted with 50 mL DCM and washed with 1 M NaOH (2×25 mL). The organic layer was dried (Na2SO4) and concentrated. FCC purification (EtOAc/DCM) gave the desired product (1.74 g, 76%). MS (ESI): mass calcd. for C15H15BrN2O, 318.04; m/z found, 319.1, 321.1 [M+H]+. 1H NMR (CDCl3): 8.42-8.39 (m, 2H), 7.31-7.26 (m, 4H), 7.00-6.99 (m, 1H), 3.84 (s, 2H), 2.11-2.07 (m, 1H), 0.43-0.40 (m, 2H), 0.36-0.33 (m, 2H).

Workup

  1. washwashed with 1 M NaOH (2×25 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customFCC purification (EtOAc/DCM)

Sources & evidence

ORD record
ord-39d5f1f410c3450bb5a509afae0490fc
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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