Sodium Bicarbonate → 5-(2-(2'-(Trifluoromethyl)biphenyl-4-yl)ethyl)indoline

HRID 710446Notes

Reaction equation

HRID 710446 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)=[CH:11][CH:10]=1.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CC(O)=O>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH2:21][CH2:20]3)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 667266155-(2-(2'-(Trifluoromethyl)biphenyl-4-yl)ethyl)-1H-indole

Product 1

HCID 667262965-(2-(2'-(Trifluoromethyl)biphenyl-4-yl)ethyl)indolineYield 75.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product of Step C (0.24 g, 0.65 mmol) was dissolved in AcOH (2 ml) and NaCNBH3 (0.082 g, 1.3 mmol) was added in portions. The mixture was stirred for 1 h and then poured into an aqueous solution of NaHCO3 and extracted with EtOAc (50 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the desired product (0.18 g, 75%), as pale paste. 1H-NMR (CDCl3) 2.81-2.94 (m, 4H); 3.0 (tr, 2H, J=7.22 Hz); 3.54 (tr, 2H, J=8.35 Hz); 6.58 (d, 1H, J=7.83 Hz); 6.84 (d, 1H, J=7.82 Hz); 6.9 (b, 1H); 7.17-7.21 (m, 3H); 7.31-7.35 (m, 2H); 7.43 (tr, 1H, J=7.65 Hz); 7.54 (tr, 1H, J=7.37 Hz); 7.72 (d, 1H, J=7.78 Hz).

Workup

  1. extractionextracted with EtOAc (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by FCC (SiO2)

Sources & evidence

ORD record
ord-26a27f8ff9a04bf9b8152cd8adeee215
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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