Tetrabutylammonium Fluoride → HCID 9922101, compound

HRID 548999Notes

Reaction equation

HRID 548999 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][N:26]=[C:21]3[CH:20]=2)=[CH:11]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[N:26]1[CH:25]=[CH:24][N:23]=[C:22]2[NH:27][C:19]([C:12]3[C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:10]([CH2:9][CH2:8][CH2:7][OH:6])[CH:11]=3)=[CH:20][C:21]=12

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22477185HCID 22477185, compound

Product 1

HCID 9922101HCID 9922101, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-{1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazine [29 g, Reference Example 3(a)] in tetrahydrofuran (500 mL) under nitrogen was treated with a solution of tetrabutylammonium fluoride in tetrahydrofuran (144 mL, 1.0M). After stirring at ambient temperature for 4 hours the reaction mixture was concentrated in vacuo. The residue was treated with water to give a solid which was filtered then washed with water and then dried to give the title compound (17.5 g) as a yellow-brown solid, m.p. 220-221° C. MS: 293 (MH+).

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was treated with water
  3. customto give a solid which
  4. filtrationwas filtered
  5. washthen washed with water
  6. customdried

Sources & evidence

ORD record
ord-d3484b6341d14b7982d73972f76b3499
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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