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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 1888603
Notes
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Reaction equation

HRID 1888603 reaction equation
[C:1]([C:3]1[N:11]=[CH:10][C:9]2[NH:8][C:7]3[N:12]=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)=[CH:18][CH:17]=4)=[CH:15][C:6]=3[C:5]=2[CH:4]=1)#[CH:2].[N:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[N+:30]=[N-:31]>CN(C)C=O.C(Cl)Cl.CO.[Cu]I>[CH2:32]([N:29]1[CH:2]=[C:1]([C:3]2[N:11]=[CH:10][C:9]3[NH:8][C:7]4[N:12]=[CH:13][C:14]([C:16]5[CH:17]=[CH:18][C:19]([CH2:22][N:23]6[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]6)=[CH:20][CH:21]=5)=[CH:15][C:6]=4[C:5]=3[CH:4]=2)[N:31]=[N:30]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 12152Benzyl azideHCID 582663926-Ethynyl-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

Product 1

HCID 445465526-(1-Benzyl-1H-1,2,3-triazol-4-yl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrroleYield 20%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 887
Methanol
Solvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-ethynyl-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (90 mg, 0.2 mmol), copper (I) iodide (4.7 mg, 0.02 mmol), and azidomethyl-benzene (36 mg, 0.27 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 residue that was purified by preparative HPLC [20-60% MeCN in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min] to afford the title compound as an off-white solid (20 mg, 20%). 1H NMR (DMSO-D6, 400 MHz): 12.30 (s, 1H), 9.16 (d, J=2.2 Hz, 1H), 8.93 (s, 2H), 8.91 (s, 1H), 8.61 (s, 1H), 7.80 (d, J=8.1 Hz, 2H), 7.40 (m, 7H), 5.69 (s, 2H), 3.49 (s, 2H), 2.36 (s, 4H), 1.57-1.46 (m, 4H), 1.40 (m, 2H). LCMS (Method D): RT=9.35 min, M+H+=500.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (15 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by preparative HPLC [20-60% MeCN in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min]

Sources & evidence

ORD record
ord-df9419bab7274a0ba16ce3cfd8185b0f
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501765B2

Reaction notes

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