Toluene → HCID 68078381, compound

HRID 476033Notes

Reaction equation

HRID 476033 reaction equation
P(Br)(Br)([Br:3])=O.[CH3:6][C:7]1[CH:8]=[C:9](O)[C:10]2[CH:15]=[N:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]=2[N:12]=1.C1(C)C=CC=CC=1>CN(C=O)C>[Br:3][C:9]1[CH:8]=[C:7]([CH3:6])[N:12]=[C:11]2[N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[CH:15][C:10]=12

Participants

5

Reactant 3

HCID 1140TolueneHCID 24613Phosphorus oxybromideHCID 178428872HCID 178428872, compound

Product 1

HCID 68078381HCID 68078381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxybromide (5.31 g, 18.54 mmol) was added to a suspension of 6-methyl-1-(phenylmethyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (3.08 g, 12.87 mmol) and toluene (25 mL). The contents were heated to reflux for 1 h, wherein 10 mL DMF were added during this process. The solvent was removed under reduced pressure. The crude residue was suspended in 30 mL water containing ice. The contents were adjusted to pH=10 by addition of sat. NaHCO3. The solid product was filtered and dried under hi-vacuum. The final product was collected as 3.55 g (91%). LCMS E-S (M+H)=302.1/304.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.61 (s, 3H), 5.65 (s, 2H), 7.16-7.35 (m, 5H), 7.48 (s, 1H), 8.12 s, 1H).

Workup

  1. temperatureThe contents were heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was removed under reduced pressure
  4. additioncontaining ice
  5. additionThe contents were adjusted to pH=10 by addition of sat. NaHCO3
  6. filtrationThe solid product was filtered
  7. customdried under hi-vacuum
  8. customThe final product was collected as 3.55 g (91%)

Sources & evidence

ORD record
ord-a6465c4b39c44019ab042fe39a48a81a
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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