Hydrochloric Acid → HCID 15454080, compound

HRID 2290118Notes

Reaction equation

HRID 2290118 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.C(=[NH:28])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].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.Cl>C1(C)C=CC=CC=1.O1CCCC1.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]>[NH2:28][C:2]1[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 10515154HCID 10515154, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 15454080HCID 15454080, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure D and using 5-bromo-3,3-dimethyl-7-ethyl-2,3-dihydro-benzofuran (Compound 9, 1.2 g, 4.72 mmol obtained substantially in accordance with J Med. Chem. 1998, 41, 1124-1137), benzophenone imine (0.94 g, 5.2 mmol), sodium-tert-butoxide (0.63 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.021 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 10 mL of anhydrous toluene, followed by hydrolysis of the intermediary imine with 2M hydrochloric acid in tetrahydrofuran, the title compound was obtained as an oil (0.7 g, 78%). 1H NMR (300 MHz, CDCl3): δ 6.37 (d, 1H, J=2.3 Hz), 6.35 (d, 1H, J=2.3 Hz), 4.17 (s, 2H), 3.15 (br s, 2H), 2.54 (q, 2H, J=7.6 Hz), 1.30 (s, 6H), 1.20 (t, 3H, J=7.6 Hz).

Workup

  1. customobtained substantially in accordance with J Med

Sources & evidence

ORD record
ord-4475fc6996ec4bf7a269c1038265662d
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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