Bromobenzene → HCID 68523991, compound

HRID 1836568Notes

Reaction equation

HRID 1836568 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([CH2:12][CH2:13][CH2:14][N:8]3[CH2:7][C@@H:6]3[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][C@H:5]23)[CH:11]=1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:26]1([NH:1][C:2]2[CH:3]=[C:4]3[C:9]4=[C:10]([CH2:12][CH2:13][CH2:14][N:8]4[CH2:7][C@@H:6]4[CH2:15][NH:16][CH2:17][C@H:5]34)[CH:11]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 634876Binap, (A+-)-HCID 23518418HCID 23518418, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 68523991HCID 68523991, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of (±)-cis-tert-butyl 2-amino-5,6,8a,9,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline-10(8H)-carboxylate (0.08 g, 0.25 mmol), bromobenzene (0.04 g, 0.27 mmol), BINAP (0.001 g, 0.0015 mmol), sodium-t-butoxide, (0.06 g, 0.65 mmol) and Pd2DBA3 (0.0005 g, 0.0005 mmol) in 10 ml of degassed toluene was heated for 16 h at 90° C. The solution was cooled and filtered through a pad of silica gel and eluted with EtOAc. The volatiles were removed under reduced pressure to afford the title compound which was used without purification. LRMS (ES)+: 406.4 (M+H)+.

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered through a pad of silica gel
  3. washeluted with EtOAc
  4. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-920f7b91d8ec4b759cf55dd630918dc5
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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