Sodium Hydroxide → HCID 22329548, compound

HRID 586239Notes

Reaction equation

HRID 586239 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[O:21]C.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:18])([F:19])[F:20])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[OH:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 10236611HCID 10236611, compound

Product 1

HCID 22329548HCID 22329548, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 7-(4-fluoro-3-methoxyphenyl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.123 g, 0.397 mmol) in chloroform (5 ml) was added boron tribromide (1.19 ml, 1.91 mmol) and the mixture was stirred under nitrogen at room temperature for 21 h. 2 M NaOH (5 ml) was added and the mixture was stirred for 5 min producing a solid which was filtered and washed with water. The filtrate was washed with dichloromethane, and the aqueous layer was neutralised with concentrated hydrochloric acid causing a solid to precipitate. The solid was filtered, washed with water and dried under a vacuum to leave 109 mg (93%) of the title compound: 1H NMR (360 MHz, DMSO-d6) δ 7.38 (1H, dd, J 8.8, 11.2 Hz), 7.60-7.64 (1H, m), 7.88 (1H, dd, J 1.9, 8.6 Hz), 9.32 (1H, s), 10.26 (1H, s); MS (ES+) m/z 299 [M+H]+.

Workup

  1. stirringthe mixture was stirred for 5 min
  2. customproducing a solid which
  3. filtrationwas filtered
  4. washwashed with water
  5. washThe filtrate was washed with dichloromethane
  6. customto precipitate
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customdried under a vacuum

Sources & evidence

ORD record
ord-3438e81f82b74944b55b92b2c7d11271
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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