Isopropylamine → HCID 18771633, compound

HRID 460213Notes

Reaction equation

HRID 460213 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[CH:10]([NH2:13])([CH3:12])[CH3:11].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:13][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 10340Sodium CarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18771633HCID 18771633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-bromo-pyridine-2-carbaldehyde (1.06 g, 5.73 mmol) in dry CH2Cl2 (30 mL) was added isopropylamine (0.51 mL, 6.02 mmol). The mixture was stirred at RT and under N2 for 30 min followed by the addition of NaBH(OAc)3 (2.42 g, 11.46 mmol) and HOAC (1.3 mL, 22.92 mmol). The resulting cloudy light-yellow solution was stirred at RT and under N2 for 15 h. A 10% solution of Na2CO3 (50 mL) was added to the mixture and stirred for 30 min. The organic phase was separated, washed with H2O, brine, dried over MgSO4 and concentrated to afford a light yellow-oil without further purification. MS m/z: 229.1 (M+H). Calc'd for C9H13BrN2: 228.03.

Workup

  1. stirringThe resulting cloudy light-yellow solution was stirred at RT and under N2 for 15 h
  2. stirringstirred for 30 min
  3. customThe organic phase was separated
  4. washwashed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto afford a light yellow-oil
  8. customwithout further purification

Sources & evidence

ORD record
ord-589afeb10fe346cfb096e2d2a26d5a30
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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