Pyrrolidine → 2-(4-Fluorophenyl)-3-[2-(1 (S)-phenylethylamino)pyridin-4-yl]-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrole

HRID 1245017Notes

Reaction equation

HRID 1245017 reaction equation
C(OC([N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[C:14]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C@H:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH3:33])[CH:26]=3)=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[NH:16][CH:17]=2)[CH2:9][CH2:8]1)=O)C=C.O1CCOCC1.N1CCCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]2[NH:16][CH:17]=[C:13]([C:10]3[CH2:11][CH2:12][NH:7][CH2:8][CH:9]=3)[C:14]=2[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C@H:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH3:33])[CH:26]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 312751,4-DioxaneHCID 575018174-(1-Allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-fluorophenyl)-3-[2-(1(S)-phenylethylamino)pyridin-4-yl]-1H-pyrrole

Product 1

HCID 575018182-(4-Fluorophenyl)-3-[2-(1 (S)-phenylethylamino)pyridin-4-yl]-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrroleYield 21.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 229 mg (0.44 mmol) of 4-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-fluorophenyl)-3-[2-(1(S)-phenylethylamino)pyridin-4-yl]-1H-pyrrole [prepared as described in step 73(iii) above] in 2.5 ml of a 10:1 by volume mixture of dioxane and water, 55 μl (0.66 mmol) of pyrrolidine and 5 mg (0.0044 mmol) of tetrakis(triphenylphosphine)palladium (0) was stirred at 0° C. for 10 minutes. At the end of this time, water was added to the reaction mixture and then this was extracted with ethyl acetate. The organic extract was washed with water and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 10:1:1 by volume mixture of ethyl acetate, methanol and isopropylamine as the eluant to give 41 mg (yield 21%) of the title compound as a pale brown amorphous solid.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by chromatography on a silica gel column
  7. additionby volume mixture of ethyl acetate, methanol and isopropylamine as the eluant

Sources & evidence

ORD record
ord-001627725d6044f091b9d92d7bfe8c7a
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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