Methyl N-(triethylammoniosulfonyl)carbamate → 2-[6-chloro-9-(3-methylbut-3-en-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile

HRID 549490Notes

Reaction equation

HRID 549490 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:26](=[CH:27][CH:28]=1)[C:12]1[NH:13][C:14]([C:16]3[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])=[N:15][C:11]=1[C:10]1[CH:9]=[CH:8][C:7]([C:29]#[C:30][C:31](O)([CH3:33])[CH3:32])=[CH:6][C:5]2=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:28]=[CH:27][C:26]2[C:12]3[N:13]=[C:14]([C:16]4[C:17]([C:18]#[N:19])=[CH:20][CH:21]=[CH:22][C:23]=4[C:24]#[N:25])[NH:15][C:11]=3[C:10]3[C:5](=[CH:6][C:7]([C:29]#[C:30][C:31]([CH3:33])=[CH2:32])=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 1784590322-(6-chloro-9-(3-hydroxy-3-methylbut-1-ynyl)-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile

Product 1

HCID 866148722-[6-chloro-9-(3-methylbut-3-en-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrileYield 78.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile from Example 40 (120 mg, 0.26 mmol) in benzene (4 mL) was added Burgess Reagent (70 mg, 0.29 mmol) and refluxed for 2 hours under N2. The resulting reaction mixture was diluted with EtOAc (20 mL). This EtOAc solution was washed with water, brine and dried over MgSO4. After removing the drying agent via filtration, the organic solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with 50/50 EtOAc/hexane) to yield 90 mg of 2-[6-chloro-9-(3-methylbut-3-en-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile as a yellow solid.

Workup

  1. temperaturerefluxed for 2 hours under N2
  2. customThe resulting reaction mixture
  3. washThis EtOAc solution was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customAfter removing the drying agent
  6. filtrationvia filtration
  7. concentrationthe organic solution was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluted with 50/50 EtOAc/hexane)

Sources & evidence

ORD record
ord-d865cf1acd9a4299b2c95498c683783d
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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