Formaldehyde → HCID 14988278, compound

HRID 1073562Notes

Reaction equation

HRID 1073562 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:18][C:19]#[CH:20])[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.[CH2:26]=O>Cl[Cu].O1CCOCC1>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:18][C:19]#[C:20][CH2:26][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 14988276HCID 14988276, compound

Product 1

HCID 14988278HCID 14988278, compoundYield 147.2%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To 100 ml of p-dioxane were added N-(3-fluoro-4-pyridinyl)-N-(2-propynyl)-1H-indol-1-amine (3.0 g), pyrrolidine (1.2 g), paraformaldehyde (4 g) and CuCl (0.3 g) and this mixture was heated to 80° C. and stirred for 3 hours. The mixture was then cooled and filtered, and the filtrate was concentrated to yield an oil (5.8 g). This material was eluted with 5% methanol/DCM on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil which solidified on standing (3.3 g). This material was then eluted with DCM on an alumina column. The desired fractions were concentrated to yield a solid (2.2 g), which was recrystallized from hexanes/ether (2:1) to yield a solid (1.5 g), m.p. 76°-78° C.

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cb3dac33713b457da70ec59ca0ece46d
Source dataset
uspto-grants-1990_11
Patent number
US04970218

Reaction notes

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