Trifluoroacetic acid → HCID 71284361, compound

HRID 1481730Notes

Reaction equation

HRID 1481730 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:11]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]4[CH2:21][CH2:22][C:23](=O)[C:16]4=[CH:15][C:14]=3[CH:13]=2)=[C:10]([CH2:25][CH3:26])[CH:9]=[C:8]([C:27]([O:29]C)=[O:28])[C:7]1=[O:31].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(C(F)(F)F)=O>ClCCCl.CC(O)=O>[CH2:25]([C:10]1[CH:9]=[C:8]([C:27]([OH:29])=[O:28])[C:7](=[O:31])[NH:6][C:11]=1[C:12]1[CH:20]=[CH:19][C:18]2[N:17]3[CH2:21][CH2:22][CH:23]([N:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)[C:16]3=[CH:15][C:14]=2[CH:13]=1)[CH3:26]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 71284929HCID 71284929, compound

Product 1

HCID 71284361HCID 71284361, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-6-(1-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-1,2-dihydropyridine-3-carboxylate (0.11 g, 0.22 mmol) in DCE (2 mL) was added pyrrolidine (80 μL, 0.88 mmol) and AcOH (30 μL). After stirring at room temperature for 1 h, NaBH(OAc)3 (0.1 g, 0.44 mmol) was added and the reaction mixture was stirred for an additional 2 h before TFA (1.5 mL) was added. After stirring for 30 min, the reaction mixture was concentrated and the crude residue was dissolved in THF (1 mL) and aqueous NaOH (2 mL, 4M) was added and the resulting mixture was heated to 60° C. for 15 h. The reaction mixture was then poured into H2O, acidified with 4M HCl, and extracted with CH2Cl2 (2×30 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo to afford a crude oil which was triturated with Et2O to afford the title compound as an orange solid (35 mg, 41% over 3 steps).

Workup

  1. additionwas added
  2. stirringAfter stirring for 30 min
  3. concentrationthe reaction mixture was concentrated
  4. dissolutionthe crude residue was dissolved in THF (1 mL)
  5. additionaqueous NaOH (2 mL, 4M) was added
  6. temperaturethe resulting mixture was heated to 60° C. for 15 h
  7. additionThe reaction mixture was then poured into H2O
  8. extractionextracted with CH2Cl2 (2×30 mL)
  9. dry with materialThe combined organic phases were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford a crude oil which
  13. customwas triturated with Et2O

Sources & evidence

ORD record
ord-ce6ce1884e624e29b8ea6c9e292343c3
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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