TBAF tetrahydrofuran → HCID 69309675, compound

HRID 1947025Notes

Reaction equation

HRID 1947025 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[C:12](=[C:13]([O:18][Si](C(C)C)(C(C)C)C(C)C)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:18])[C:12]=3[CH:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 69311915HCID 69311915, compound

Product 1

HCID 69309675HCID 69309675, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-methylsulfanyl-pyrimidin-4-yl)-4-triisopropylsilanyloxy-1H-indole (7.75 g) in THF (50 mL) was mixed with TBAF/THF (8 mL) and allowed to stir at RT for 2 h, then quenched with water. The aqueous layer was acidified with 1N HCl. The resulting solid was filtered, washed with water and dried at 50° C. in vacuo overnight to yield 1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indol-4-ol (4.5 g).

Workup

  1. customquenched with water
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customdried at 50° C. in vacuo overnight

Sources & evidence

ORD record
ord-2b87dc954cf84f0e8e3df7071509da71
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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