Sodium Hydroxide → HCID 67466688, compound

HRID 1046005Notes

Reaction equation

HRID 1046005 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[I:9].[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[OH:18].C1CCN2C(=NCCC2)CC1.[OH-].[Na+]>CN1C(=O)CCC1>[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[O:18][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[I:9]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 949522,5-DifluorophenolHCID 229365964-Chloro-3-iodopyridin-2-amine

Product 1

HCID 67466688HCID 67466688, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

4-chloro-3-iodopyridin-2-amine (3.00 g, 11.79 mmol), 2,5-difluoro phenol (4.60 g, 35.4 mmol), DBU (1.777 ml, 11.79 mmol) were combined in NMP (15 mL) and solution was stirred at 170° C. for 6 h under microwave irradiation. The crude reaction mixture was poured into 1N NaOH solution (70 mL), the resultant suspension was filtered, washed with water (5×10 mL) and dried to afford crude product which was purified by silica gel chromatography (EtOAc-hexanes) to afford 4-(2,5-difluorophenoxy)-3-iodopyridin-2-amine as white solid. (2.55 g, 62.1% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.74 (d, J=7.6 Hz, 1H), 7.47 (m, 1H), 7.28 (m, 1H), 7.18 (On, 1H), 6.25 (br s, 2H), 5.88 (dd, J=5.6 Hz, 1H); MS (ESI) m/z: 349.03 (M+H+).

Workup

  1. customThe crude reaction mixture
  2. filtrationthe resultant suspension was filtered
  3. washwashed with water (5×10 mL)
  4. customdried
  5. customto afford crude product which
  6. customwas purified by silica gel chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-967b7d08e0134336968bdd19e3fcb8ba
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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