Diisopropylethylamine → 4-(2,5-Dimethyl-1H-indol-4-yl)-1-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-butan-2-ol

HRID 40647Notes

Reaction equation

HRID 40647 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH2:11][CH2:12][CH:13]1[CH2:15][O:14]1)[C:7]([CH3:16])=[CH:6][CH:5]=2.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[N:27]1[CH2:34][C@H:33]2[NH:35][CH2:36][C@@H:28]1[CH2:29][CH:30]=[CH:31][CH2:32]2.CCN(C(C)C)C(C)C>C(O)C>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH2:11][CH2:12][CH:13]([OH:14])[CH2:15][N:35]1[CH2:36][CH:28]3[N:27]([C:18]4[CH:19]=[CH:20][C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH:17]=4)[CH2:34][CH:33]1[CH2:32][CH:31]=[CH:30][CH2:29]3)[C:7]([CH3:16])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59686818Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-eneHCID 866191522,5-Dimethyl-4-(2-oxiranyl-ethyl)-1H-indole

Product 1

HCID 692351594-(2,5-Dimethyl-1H-indol-4-yl)-1-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-butan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,5-Dimethyl-4-(2-oxiranyl-ethyl)-1H-indole (50 mg, 0.23 mmol), Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (45 mg, 0.17 mmol), DIPEA (0.1 mL, 0.55 mmol), ethanol (3 mL) were heated for 900 sec. at 120° C. in a μW reaction tube. The solvent was evaporated under reduced pressure to yield a crude solid that was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate] to yield the title compound as a residue.

Workup

  1. customat 120° C.
  2. customThe solvent was evaporated under reduced pressure
  3. customto yield a crude solid
  4. customthat was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate]

Sources & evidence

ORD record
ord-80c298e12a7e429eb7839cbb6696f7f3
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Reaction notes

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