1-Chloro-4-iodobenzene → HCID 70979692, compound

HRID 1485483Notes

Reaction equation

HRID 1485483 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=3[NH:9][C:10]([CH3:13])([CH3:12])[CH2:11][C:5]2=[N:4][N:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.CC([O-])(C)C.[Na+]>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:9]2[C:10]([CH3:13])([CH3:12])[CH2:11][C:5]3=[N:4][N:3]=[C:2]([CH3:1])[N:6]3[C:7]3[CH:17]=[CH:16][CH:15]=[CH:14][C:8]2=3)=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 125101-Chloro-4-iodobenzeneHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 23676156Sodium t-butoxideHCID 70979284HCID 70979284, compound

Product 1

HCID 70979692HCID 70979692, compound

Conditions

Temperature
90 °C

Procedure

A disposable tube was charged with 1,5,5-trimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (150 mg, 0.657 mmol), 1-chloro-4-iodobenzene (204 mg, 0.854 mmol), RuPhos precat. (23.94 mg, 0.033 mmol), sodium 2-methylpropan-2-olate (126 mg, 1.314 mmol), and a stirbar before being evacuated and purged with nitrogen three times. Toluene (3 mL, 0.5 M) was added, and the mixture was stirred at 90° C. 48 h. The mixture was cooled, diluted with ethyl acetate, filtered, and purified by reverse phase HPLC to yield the title compound as an off-white amorphous solid.

Workup

  1. custompurged with nitrogen three times
  2. additionToluene (3 mL, 0.5 M) was added
  3. custom48 h
  4. temperatureThe mixture was cooled
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-af1311636a3146c1af03d48475b053f0
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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