Triphenylphosphine → 1-cyclopropyl-3-((1-isopentyl-5-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one

HRID 632868Notes

Reaction equation

HRID 632868 reaction equation
[CH2:1]([N:6]1[C:14]2[C:9](=[N:10][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:12][CH:13]=2)[N:8]=[C:7]1[CH2:19]O)[CH2:2][CH:3]([CH3:5])[CH3:4].[CH:21]1([N:24]2[C:32]3[CH:31]=[CH:30][N:29]=[CH:28][C:27]=3[NH:26][C:25]2=[O:33])[CH2:23][CH2:22]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1COCC1>[CH:21]1([N:24]2[C:32]3[CH:31]=[CH:30][N:29]=[CH:28][C:27]=3[N:26]([CH2:19][C:7]3[N:6]([CH2:1][CH2:2][CH:3]([CH3:4])[CH3:5])[C:14]4[C:9]([N:8]=3)=[N:10][C:11]([C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=4)[C:25]2=[O:33])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 223493611-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-oneHCID 67991823(1-isopentyl-5-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-2-yl)methanol

Product 1

HCID 679917831-cyclopropyl-3-((1-isopentyl-5-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-oneYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (1-isopentyl-5-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-2-yl)methanol 44-3 (1.0 g, 3.5 mmol (73% purity)), 1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one 10-d (731.8 mg, 4.2 mmol) and triphenylphosphine (1.1 g, 4.2 mmol) in 24 ml dry THF was added (E)-diisopropyl diazene-1,2-dicarboxylate (1.0 ml, 5.2 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was evaporated to dryness and purified by preparative column chromatography to obtain 44 as a white solid (578.0 mg, 37%). m/z=445 (M+H)+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.02 (m, J=6.50 Hz, 8H) 1.13-1.24 (m, 2 H) 1.48-1.64 (m, 2 H) 1.73 (dquin, J=13.19, 6.49, 6.49, 6.49, 6.49 Hz, 1 H) 2.92 (tt, J=6.81, 3.48 Hz, 1 H) 4.35-4.52 (m, 2 H) 5.41 (s, 2 H) 7.13 (d, J=5.27 Hz, 1 H) 7.61 (d, J=8.28 Hz, 1 H) 7.79 (d, J=8.28 Hz, 1 H) 8.34 (d, J=5.27 Hz, 1 H) 8.68 (s, 1 H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by preparative column chromatography

Sources & evidence

ORD record
ord-e1f97244c05f4ca0847b5340867f6bda
Source dataset
uspto-grants-2016_04
Patent number
US09321767B2

Reaction notes

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