1-Chloro-4-iodobenzene → HCID 70978954, compound
Reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[NH:9][CH:10]([CH3:12])[CH2:11][C:5]2=[N:4][N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.CC([O-])(C)C.[Na+]>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:9]2[CH:10]([CH3:12])[CH2:11][C:5]3=[N:4][N:3]=[C:2]([CH3:1])[N:6]3[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]2=3)=[CH:20][CH:19]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
A disposable tube was charged with 1,5-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (69 mg, 0.322 mmol), 1-chloro-4-iodobenzene (100 mg, 0.419 mmol), RuPhos precat. (11.73 mg, 0.016 mmol), dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (7.51 mg, 0.016 mmol), sodium 2-methylpropan-2-olate (61.9 mg, 0.644 mmol), and a stirbar before being evacuated and purged with nitrogen three times. Toluene (1 mL, 0.4 M) was added, and the mixture was stirred at 90° C. 36 h. The mixture was cooled, diluted with ethyl acetate, filtered, and concentrated before being purified by silica gel chromatography (eluting with methylene chloride/methanol/1% ammonium hydroxide) and reverse phase HPLC to yield the title compound as a white amorphous solid (0.011 g, 0.034 mmol, 11%).
Workup
- custompurged with nitrogen three times
- additionToluene (1 mL, 0.4 M) was added
- custom36 h
- temperatureThe mixture was cooled
- additiondiluted with ethyl acetate
- filtrationfiltered
- concentrationconcentrated
- custombefore being purified by silica gel chromatography (eluting with methylene chloride/methanol/1% ammonium hydroxide)
Sources & evidence
- ORD record
- ord-e38c190e48d54be991775f406772c40d
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422292B2
Reaction notes
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