Ethanol → 4-[3-Hydroxy-4-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-butyl]-6-methoxy-1H-indole-2-carboxylic acid methyl ester

HRID 40646Notes

Reaction equation

HRID 40646 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([CH2:14][CH2:15][CH:16]1[CH2:18][O:17]1)[CH:10]=[C:9]([O:19][CH3:20])[CH:8]=2)=[O:4].[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[N:31]1[CH2:38][C@H:37]2[NH:39][CH2:40][C@@H:32]1[CH2:33][CH:34]=[CH:35][CH2:36]2.CCN(C(C)C)C(C)C.C(O)C>ClCCl>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([CH2:14][CH2:15][CH:16]([OH:17])[CH2:18][N:39]1[CH2:40][CH:32]3[N:31]([C:22]4[CH:23]=[CH:24][C:25]5[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH:21]=4)[CH2:38][CH:37]1[CH2:36][CH:35]=[CH:34][CH2:33]3)[CH:10]=[C:9]([O:19][CH3:20])[CH:8]=2)=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 59686818Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-eneHCID 866191516-Methoxy-4-(2-oxiranyl-ethyl)-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 692337534-[3-Hydroxy-4-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-butyl]-6-methoxy-1H-indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-4-(2-oxiranyl-ethyl)-1H-indole-2-carboxylic acid methyl ester (120 mg, 0.43 mmol), Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (114 mg, 0.43 mmol), DIPEA (0.2 mL, 1.13 mmol), ethanol (3 mL), dichloromethane (2 mL) were heated for 1200 sec. at 130° C. in a μW reaction tube. The solvent was evaporated under reduced pressure to yield a crude solid which was then purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate] to yield the title compound as a residue.

Workup

  1. customat 130° C.
  2. customThe solvent was evaporated under reduced pressure
  3. customto yield a crude solid which
  4. customwas then purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate]

Sources & evidence

ORD record
ord-900ab4f2d20f402eadc80f38d5192c8a
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Reaction notes

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