Ammonia → HCID 131723995, compound

HRID 1359334Notes

Reaction equation

HRID 1359334 reaction equation
[CH2:1]([C:8]1[C:13](Br)=[CH:12][CH:11]=[C:10]([C:15]#[C:16][CH2:17][O:18][CH3:19])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([C:22]1([OH:30])[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1)#[CH:21].C(N(CC)CC)C.N>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.C(OCC)(=O)C.CN(C)C=O>[CH2:1]([C:8]1[C:13]([C:21]#[C:20][C:22]2([OH:30])[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[CH:12][CH:11]=[C:10]([C:15]#[C:16][CH2:17][O:18][CH3:19])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 85784319HCID 85784319, compound

Product 1

HCID 131723995HCID 131723995, compoundYield 57.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next, a mixture of 170 mg of 2-benzyl-3-bromo-6-(3-methoxy-1-propinyl)pyridine, 90 mg of 3-ethynyl-3-quinuclidinol, 30 mg of tetrakis(triphenylphosphine)palladium(0), 1 mg of cuprous iodide, 0.22 ml of triethylamine and 1 ml of N,N-dimethylformamide was stirred for 2 hours in an oil bath kept at 85° C. in a nitrogen atmosphere. Ethyl acetate and aqueous dilute ammonia were added to the reaction solution to separate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using NH-silica gel to elute with 20-100% ethyl acetate/hexane and then with 2.5% methanol/ethyl acetate, to give 120 mg of the target compound.

Workup

  1. customkept at 85° C. in a nitrogen atmosphere
  2. customto separate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washto elute with 20-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-962180d7e77e43238ea132d7197d8fac
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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