Iodine → 5-Iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8h-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

HRID 1642520Notes

Reaction equation

HRID 1642520 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[CH:21]=[C:20]([Si](C)(C)C)[C:11]3[C:12]4[C:13]([NH:19][C:10]=3[C:9]2=[O:26])=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=4)=[CH:5][CH:4]=1.[I:29]I>C(O)C.C(Cl)Cl.F[B-](F)(F)F.[Ag+]>[I:29][C:20]1[C:11]2[C:12]3[C:13]([NH:19][C:10]=2[C:9](=[O:26])[N:8]([CH2:7][C:6]2[CH:27]=[CH:28][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:21]=1)=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3

Participants

6

Reactant 2

HCID 807IodineHCID 588800657-(4-methoxybenzyl)-3-methyl-5-trimethylsilyl-7,9-dihydro-8H-pyrido[4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

Product 1

HCID 588800935-Iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8h-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 2 L round bottom flask, 7-(4-methoxybenzyl)-3-methyl-5-trimethylsilyl-7,9-dihydro-8H-pyrido[4′,3′:4,5]pyrrolo[2,3-b]pyridin-8-one (18.6 g, 47.505 mmol) was suspended in ethanol (1 L) and DCM (150 mL), then cooled in an ice bath. To the cooled mixture was added silver tetrafluoroborate (AgBF4, 10.17 g, 52.255 mmol) and after 15 minutes of stirring, iodine (18.08 g, 71.257 mmol) was added. The reaction was stirred at 0° C. for one hour followed by five hours at ambient temperature. The crude yellow solid was collected by filtration, suspended in 10% wt Na2S2O3 (700 mL) and stirred for 1 h. The solid was collected by filtration and again washed with 10% wt Na2S2O3. The product (light yellow solid) was collected by filtration, washed with water and diethyl ether and dried under high vacuum. The material was taken forward without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.59 (s, 3 H) 3.81 (s, 3 H) 5.26 (s, 2 H) 6.90 (d, J=8.84 Hz, 2 H) 7.34 (d, J=8.59 Hz, 2 H) 7.44 (s, 1 H) 8.51 (s, 1 H) 8.92 (s, 1 H). ESI-MS: m/z 446.2 (M+H)+.

Workup

  1. stirringThe reaction was stirred at 0° C. for one hour
  2. waitfollowed by five hours at ambient temperature
  3. filtrationThe crude yellow solid was collected by filtration
  4. stirringstirred for 1 h
  5. filtrationThe solid was collected by filtration
  6. washagain washed with 10% wt Na2S2O3
  7. filtrationThe product (light yellow solid) was collected by filtration
  8. washwashed with water and diethyl ether
  9. customdried under high vacuum
  10. customThe material was taken forward without further purification

Sources & evidence

ORD record
ord-73399f7b2b3540ecbcf94a44414c1888
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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