Indene → HCID 22633316, compound

HRID 2417399Notes

Reaction equation

HRID 2417399 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)(C)(C)C.[OH:17][C:18]1[CH:23]=[C:22]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=2[O:32][CH3:33])[C:21]([CH:34]=O)=[CH:20][C:19]=1[O:36][CH3:37].[CH2:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39]1.[O-]S(C(F)(F)F)(=O)=O.[In+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(#N)C>[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:12](=[CH:13][CH:14]=1)[NH:15][CH:34]([C:21]1[C:22]([C:24]3[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=3[O:32][CH3:33])=[CH:23][C:18]([OH:17])=[C:19]([O:36][CH3:37])[CH:20]=1)[CH:39]1[CH2:40][C:41]3[C:46]([CH:38]21)=[CH:45][CH:44]=[CH:43][CH:42]=3

Participants

6

Reactant 4

HCID 7219IndeneHCID 2734680Indium(III) trifluoromethanesulfonateHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 22633129HCID 22633129, compound

Product 1

HCID 22633316HCID 22633316, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

(4-Amino-benzyl)-carbamic acid tert-butyl ester (307 mg, 1.4 mmole) was dissolved in acetonitrile (approx. 5 mL). The solution was treated with 5-hydroxy-4,2′,6′-trimethoxy-biphenyl-2-carbaldehyde (390 mg, 1.4 mmole) and indene (157 mg, 1.4 mmole). Indium triflate (1.2 g, 2.2 mmole) was added and the reaction was heated at 70° C. for 18 hours to give 6-(2-Aminomethyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-4,2′,6′-trimethoxy-biphenyl-3-ol which was then purified using reverse phase HPLC. Mass spectrum 491 (M−17); in the presence of 0.1M ammonium acetate 507 (M−1) observed for negative ion mode.

Sources & evidence

ORD record
ord-a806eac48bd64a1695cd32c1b25569b0
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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