Diisopropylethylamine → (S)-1-(1-Methyl-1H-indol-4-yloxy)-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-2-ol

HRID 40635Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

(S)-1-Methyl-4-oxiranylmethoxy-1H-indole (50 mg, 0.25 mmol) and Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (50 mg, 0.189 mmol) were placed in a μW tube with ethanol (2 ml), DIPEA (100 μL, 0.576 mmol) and heated to 120° C. for 900 sec. The solvent was evaporated from the reaction mixture and the residue was purified via flash chromatography (gradient 30% to 100% ethyl acetate/heptane) to yield the title compound as a residue.

Workup

customThe solvent was evaporated from the reaction mixture
customthe residue was purified via flash chromatography (gradient 30% to 100% ethyl acetate/heptane)

Sources & evidence

ORD record: ord-ddd004fecaf94130b2abbe57112a1163
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530475B2

Reaction notes

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