Pyrrolidine → HCID 22641503, compound

HRID 2415491Notes

Reaction equation

HRID 2415491 reaction equation
Cl.Cl[C:3]1[N:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:16][C:17]([CH3:21])=[N:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH:73]1[CH2:77][CH2:76][CH2:75][CH2:74]1>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:21][C:17]1[CH:16]=[C:15]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[C:14]2[C:19](=[CH:20][C:11]([O:10][CH2:9][C:6]3[CH:7]=[N:8][C:3]([N:73]4[CH2:77][CH2:76][CH2:75][CH2:74]4)=[CH:4][CH:5]=3)=[CH:12][CH:13]=2)[N:18]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 22641487HCID 22641487, compound

Product 1

HCID 22641503HCID 22641503, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 98.5 mg (0.25 mmol) of 7-(6-chloro-pyridin-3-ylmethoxy)-2-methyl-4-pyrrolidin-1-yl-quinoline hydrochloride, product of example 56, 16 mg (0.03 mmol) of BINAP, 2.8 mg (0.01 mmol) of Pd(II) acetate, and 99 mg (1 mmol) of sodium tert-butylate in toluene (4.5 ml) was treated at RT with 36 mg (0.5 mmol) of pyrrolidine and then heated at reflux under an argon atmosphere for 4 h. The reaction mixture was cooled to RT, diluted with methylene chloride (10 ml), and then filtered. The filtrate was concentrated in vacuo, the residue triturated with ether, filtered off by suction and dried in a high vacuum to give 88 mg (84%) of the 2-methyl-4-pyrrolidin-1-yl-7-(6-pyrrolidin-1-yl-pyridin-3-ylmethoxy)-quinoline as a white solid. ISP mass spectrum, m/e: 389.3 (M+1 calculated for C24H28N4O: 389).

Workup

  1. temperatureheated
  2. temperatureat reflux under an argon atmosphere for 4 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue triturated with ether
  6. filtrationfiltered off by suction
  7. customdried in a high vacuum

Sources & evidence

ORD record
ord-137a6b79924d4573a2971f7f56e3ff39
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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