1,1-Dimethylhydrazine → HCID 11804817, compound
Reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].Br[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.O(C(C)(C)C)[Li]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:4])[NH:3][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
7
Conditions
- Temperature
- 80 °C
Procedure
N,N-Dimethylhydrazine (2.0 equiv., 1.0 mmol, 0.075 mL), bromobenzene (1 equiv., 0.5 mmol, 0.05 mL), Pd2(DBA)3 (0.025 equiv., 0.0125 mmol, 12 mg), BINAP (0.05 equiv., 0.025 mmol, 16 mg), LiOtBu (1.2 equiv., 0.6 mmol, 48 mg) and toluene (5 mL) were added to an oven dried test tube which was capped with a septum and purged briefly with argon (˜1 min.), and then heated to 80° C. under argon for 18 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (10% EtOAc/Hex) to give the title product as a yellow oil (17 mg, 0.12 mmol, 24% yield).
Workup
- customdried test tube which
- customwas capped with a septum
- custompurged briefly with argon (˜1 min.)
- temperatureThe reaction was then cooled to room temperature
- additiondiluted with Et2O (2 mL)
- filtrationfiltered through Celite
- concentrationconcentrated under vacuum
- customThe crude mixture was purified by flash column chromatography (10% EtOAc/Hex)
Sources & evidence
- ORD record
- ord-2bab5db622054df7a33cea1d0e7e1257
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235936B1
Reaction notes
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