Toluene → HCID 68078381, compound

HRID 1522425Notes

Reaction equation

HRID 1522425 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, 3 H), 5.65 (s, 2 H), 7.16-7.35 (m, 5 H), 7.48 (s, 1 H), 8.12 s, 1 H).

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-56d65b042f144f83add5ddba01018b88
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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