Dichloromethane → 7-Fluoro-3,4,4a,5-tetrahydro-2H-indeno[1,2-b]pyridine

HRID 2040745Notes

Reaction equation

HRID 2040745 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH2:5].[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[CH2:11][CH2:10]2.C(N(CC)CC)C.C(Cl)Cl>CN(C=O)C.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12]1=[N:5][CH2:4][CH2:3][CH2:2][CH:11]1[CH2:10]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 787023-BromopropylamineHCID 1365375-Fluoro-1-indanone

Product 1

HCID 140750577-Fluoro-3,4,4a,5-tetrahydro-2H-indeno[1,2-b]pyridine

Reagents, catalysts & solvents 2

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromopropylamine (4.7 g. 21.7 mmole) and 5-Fluoro-1-indanone (2.5 g, 16.7 mmole) were dissolved in 50 ml DMF and the reaction was cooled to 0° C. Triethylamine (13.5 g, 133 mmole) was added. 20 ml DCM was also added to help with the stirring. Titanium chloride (1M in DCM, 15 ml) was then added and the ice bath was removed. The reaction was stirred at room temperature overnight. 200 ml ether was added and the reaction was filtered though a Celite cake. The filtrate was concentrated to dryness under vacuum. The residue was dissolved in 200 ml ether and washed with brine (2×200 ml). The organic layer was dried over sodium sulfate and concentrated to dryness. 2.6 g Black oil was obtained and it was used in next step without further purification.

Workup

  1. customthe ice bath was removed
  2. addition200 ml ether was added
  3. filtrationthe reaction was filtered though a Celite cake
  4. concentrationThe filtrate was concentrated to dryness under vacuum
  5. dissolutionThe residue was dissolved in 200 ml ether
  6. washwashed with brine (2×200 ml)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated to dryness
  9. custom2.6 g Black oil was obtained
  10. customit was used in next step without further purification

Sources & evidence

ORD record
ord-36384d1985414c868f5e2a91fc2bb6bb
Source dataset
uspto-grants-2013_11
Patent number
US08580956B2

Reaction notes

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