Indene → HCID 22633173, compound

HRID 2417398Notes

Reaction equation

HRID 2417398 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[C:25]([O:26][CH3:27])=[CH:24][C:21]([CH:22]=O)=[C:20]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])[CH:19]=1.[CH2:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38]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:22]([C:21]1[C:20]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])=[CH:19][C:18]([OH:17])=[C:25]([O:26][CH3:27])[CH:24]=1)[CH:38]1[CH2:39][C:40]3[C:45]([CH:37]21)=[CH:44][CH:43]=[CH:42][CH:41]=3

Participants

6

Reactant 4

HCID 7219IndeneHCID 2734680Indium(III) trifluoromethanesulfonateHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 22633232HCID 22633232, compound

Product 1

HCID 22633173HCID 22633173, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

(4-Amino-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.9 mmole) was dissolved in acetonitrile (5 mL). The solution was treated with 4-Hydroxy-5-methoxy-2-(2-methoxy-phenoxy)-benzaldehyde (250 mg, 0.9 mmole) and indene (130 mg, 1.1 mmole). Indium triflate (600 mg, 1.1 mmole) was added and the reaction was heated at 70° C. for 18 hours to give 4-(2-Aminomethyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-2-methoxy-5-(2-methoxy-phenoxy)-phenol which was then purified using reverse phase HPLC.

Sources & evidence

ORD record
ord-abc99f78d9ee4b5eace8553df3305c01
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

Loading…