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Dimethylformamide → 3,4-Bis(benzyloxy)-6-[(4-methoxycyclohex-1-en-1-yl)ethynyl]pyridazine

HRID 927073
Notes
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Reaction equation

HRID 927073 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH:10]([O:13][CH3:14])[CH2:9][CH:8]=1)(=O)=O.C(N(CC)CC)C.CN(C)C=O.[CH2:29]([O:36][C:37]1[N:38]=[N:39][C:40]([C:51]#[CH:52])=[CH:41][C:42]=1[O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1.[Cu]I.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>[CH2:29]([O:36][C:37]1[N:38]=[N:39][C:40]([C:51]#[C:52][C:7]2[CH2:12][CH2:11][CH:10]([O:13][CH3:14])[CH2:9][CH:8]=2)=[CH:41][C:42]=1[O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 583380034-Methoxy-1-cyclohexenyl TrifluoromethanesulfonateHCID 866770253,4-Bis(benzyloxy)-6-ethynylpyridazine2×

Product 1

HCID 712703263,4-Bis(benzyloxy)-6-[(4-methoxycyclohex-1-en-1-yl)ethynyl]pyridazineYield 97.9%

Reagents, catalysts & solvents

3
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A microwave reaction vial was charged with 4-methoxycyclohex-1-enyl trifluoromethanesulfonate (1069 mg, 4.11 mmol), copper(I) iodide (16.83 mg, 0.09 mmol), tetrakis(triphenylphosphine)palladium(0) (54.6 mg, 0.05 mmol), triethylamine (1432 μl, 10.27 mmol) and dry N,N-dimethylformamide (6849 μl). The reaction was evacuated and purged with nitrogen and a solution of 3,4-bis(benzyloxy)-6-ethynylpyridazine (Intermediate 5; 650 mg, 2.06 mmol) in dry tetrahydrofuran (3 ml) was added before the whole was then stirred in the microwave at 70° C. for 1 hour. Upon cooling, the resulting mixture was partitioned between ethyl acetate and water and the organic extracts were washed with water and brine, dried (MgSO4), filtered and concentrated to afford a brown oil. This was purified by chromatography on silica eluting with 0-75% ethyl acetate in petrol to give 3,4-bis(benzyloxy)-6-[(4-methoxycyclohex-1-en-1-yl)ethynyl]pyridazine (Intermediate 20) as a brown oil (860 mg, 85%).

Workup

  1. customA microwave reaction
  2. customThe reaction was evacuated
  3. custompurged with nitrogen
  4. temperatureUpon cooling
  5. customthe resulting mixture was partitioned between ethyl acetate and water
  6. washthe organic extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a brown oil
  11. customThis was purified by chromatography on silica eluting with 0-75% ethyl acetate in petrol

Sources & evidence

ORD record
ord-c86c96b2b67f4e3f9745ac87c2e7df04
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290456B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes