Tetrabutylammonium Fluoride → HCID 59427354, compound

HRID 1042897Notes

Reaction equation

HRID 1042897 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=2)=[N:4][N:3]=1.C[Si](C)(C)[C:21]1[O:29][C:28]2[C:23](=[N:24][CH:25]=[CH:26][C:27]=2[S:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH:22]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CC(O)CC>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([NH:37][C:34]3[CH:33]=[CH:32][C:31]([S:30][C:27]4[CH:26]=[CH:25][N:24]=[C:23]5[CH:22]=[CH:21][O:29][C:28]=45)=[CH:36][CH:35]=3)=[N:3][N:4]=2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 67316641HCID 67316641, compoundHCID 86628670HCID 86628670, compound

Product 1

HCID 59427354HCID 59427354, compound

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with 1-chloro-4-(5-chloropyridin-2-yl)phthalazine (0.095 g, 0.34 mmol), 4-(2-(trimethylsilyl)furo[3,2-b]pyridin-7-ylthio)benzenamine (0.090 g, 0.29 mmol) and 2-butanol (3.0 mL). The system was flushed with argon, and the tube was sealed. The mixture stirred at 100° C. for 2 h. LC-MS showed starting aniline and hydrolyzed phthalazine, so 90 mg of chlorophthalazine was added and the reaction was stirred for 1 h at 100° C. The reaction was concentrated, re-dissolved in THF, and TBAF (1.0 M in THF) (0.29 ml, 0.29 mmol) was added. The reaction was stirred at 60° C. overnight. The reaction was concentrated and purified via Gilson HPLC (gradient elution 10-90% MeCN:H2O). The clean fractions were partitioned between DCM and saturated sodium bicarbonate solution and the layers were separated. The aqueous layer was extracted with DCM and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford 4-(5-chloropyridin-2-yl)-N-(4-(furo[3,2-b]pyridin-7-ylthio)phenyl)phthalazin-1-amine as a yellow solid. MS: M+H+=482.1.

Workup

  1. customThe system was flushed with argon
  2. customthe tube was sealed
  3. additionwas added
  4. stirringthe reaction was stirred for 1 h at 100° C
  5. concentrationThe reaction was concentrated
  6. dissolutionre-dissolved in THF
  7. stirringThe reaction was stirred at 60° C. overnight
  8. concentrationThe reaction was concentrated
  9. custompurified via Gilson HPLC (gradient elution 10-90% MeCN:H2O)
  10. customThe clean fractions were partitioned between DCM and saturated sodium bicarbonate solution
  11. customthe layers were separated
  12. extractionThe aqueous layer was extracted with DCM
  13. dry with materialthe combined organic layers were dried with sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-e8dcde5a87c041e3917b080c5ec41fbf
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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