Cesium carbonate → HCID 53328344, compound

HRID 1190875Notes

Reaction equation

Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1OCCOC1>[CH3:8][C:7]1[C:2]([N:31]2[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]2)=[C:3]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In a oven-dried flask and under a nitrogen atmosphere, were placed tert-butyl N-[(2-bromo-3-methyl-5-nitrophenyl)methyl]carbamate (150 mg, 0.43 mmol), (+/−) BINAP (14 mg, 0.05 eq), Cs2CO3 (196 mg, 1.4 eq), Pd2dba3 (10 mg, 0.05 eq) and 3 mL of dry 1,4-dioxanne. N-Methylpiperazine (58 μL, 1.2 eq) was added and the mixture was stirred at 90° C. for 16 h. The solution was filtered through a celite pad and evaporated. The residue was purified by flash chromatography on silica gel (DCM/MeOH/NEt3//9/1/0.1) to yield expected compound as a pale brown solid (100 mg, 64% yield). m/z (ESI) 365.2 [M+H]+;

Workup

customIn a oven-dried flask and under a nitrogen atmosphere, were placed
filtrationThe solution was filtered through a celite pad
customevaporated
customThe residue was purified by flash chromatography on silica gel (DCM/MeOH/NEt3//9/1/0.1)

Sources & evidence

ORD record: ord-d1c0e0ebf34a4ceebc561b6543977390
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680095B2

Reaction notes

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