Benzyl azide → 6-(1-Benzyl-1H-1,2,3-triazol-4-yl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1506069Notes

Reaction equation

[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[C:5]([C:10]2[C:11](F)=[N:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)[CH:15]=2)[CH:4]=1)#[CH:2].[N:30]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[N+:31]=[N-:32]>CN(C)C=O.C(Cl)Cl.CO.[Cu]I>[CH2:33]([N:30]1[CH:2]=[C:1]([C:3]2[N:8]=[CH:7][C:6]3[NH:9][C:11]4[N:12]=[CH:13][C:14]([C:16]5[CH:21]=[CH:20][C:19]([CH2:22][N:23]6[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]6)=[CH:18][CH:17]=5)=[CH:15][C:10]=4[C:5]=3[CH:4]=2)[N:32]=[N:31]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6′-ethynyl-2-fluoro-5-(4-piperidin-1-ylmethylphenyl)-[3,4]bipyridinyl-3′-ylamine (60 mg, 0.16 mmol), copper (I) iodide (3.0 mg, 0.016 mmol), and azidomethylbenzene (29 mg, 0.22 mmol) in N,N-dimethylformamide (2 mL) was heated at 60° C. for 2 h. The cooled reaction mixture was diluted with DCM (20 mL) and methanol (2 mL) and washed with water (15 mL). The organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford a brown residue that was taken to the next step without purification.

Workup

customThe cooled reaction mixture
washwashed with water (15 mL)
customThe organic phase was separated
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated in vacuo
customto afford a brown residue that
customwas taken to the next step without purification

Sources & evidence

ORD record: ord-1387c88a2b6e42408e23986f7c2819ac
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216980B2

Reaction notes

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