Methyl iodide → 4'-(5-fluoro-2,3-dihydroindole-1-carbonyl)-1'-methyl-4-(2-oxo-2,3-dihydroimidazo[4,5-b]-pyridin-1-yl)-3,4,5,6-tetrahydro-2H,1'H-[1,2']bipyridinyl-6'-one

HRID 2059984Notes

Reaction equation

HRID 2059984 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:14]=[C:15]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[NH:28][C:27]4=[O:35])[CH2:22][CH2:21]3)[NH:16][C:17](=[O:19])[CH:18]=1)=[O:12])[CH2:6][CH2:5]2.[C:36](=O)([O-])[O-].[Cs+].[Cs+].CI>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:14]=[C:15]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[NH:28][C:27]4=[O:35])[CH2:22][CH2:21]3)[N:16]([CH3:36])[C:17](=[O:19])[CH:18]=1)=[O:12])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 426133804'-(5-fluoro-2,3-dihydroindole-1-carbonyl)-4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H,1'H-[1,2']bipyridinyl-6'-one

Product 1

HCID 426133814'-(5-fluoro-2,3-dihydroindole-1-carbonyl)-1'-methyl-4-(2-oxo-2,3-dihydroimidazo[4,5-b]-pyridin-1-yl)-3,4,5,6-tetrahydro-2H,1'H-[1,2']bipyridinyl-6'-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

50 mg (0.11 mmol) of 4′-(5-fluoro-2,3-dihydroindole-1-carbonyl)-4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H,1′H-[1,2′]bipyridinyl-6′-one were placed in 0.50 mL DMSO at RT. To this were added 88 mg (0.27 mmol) caesium carbonate and the mixture was stirred for 15 min. Then a solution of 6.5 μL (0.11 mmol) methyl iodide in DMSO was added and the mixture was stirred for 2 h at RT. More methyl iodide was added (3.3 μL, 0.055 mmol) and the mixture was stirred for a further 2 h at RT. The reaction mixture was purified by preparative HPLC. The fractions containing the product were combined and lyophilised.

Workup

  1. stirringthe mixture was stirred for 2 h at RT
  2. stirringthe mixture was stirred for a further 2 h at RT
  3. customThe reaction mixture was purified by preparative HPLC
  4. additionThe fractions containing the product

Sources & evidence

ORD record
ord-9129089339894562b1fc97775357f95d
Source dataset
uspto-grants-2012_10
Patent number
US08278336B2

Reaction notes

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