Tetrabutylammonium Fluoride → 8-fluoro-1-[(3-fluoro-4-hydroxycyclohexyl)amino]-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971020Notes

Reaction equation

HRID 1971020 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[C:28]3[C:27]4[CH:26]=[C:25]([F:29])[CH:24]=[CH:23][C:22]=4[NH:21][C:20]=3[C:19]([C:30]#[N:31])=[CH:18][N:17]=2)[CH2:11][CH:10]1[F:32])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:29][C:25]1[CH:24]=[CH:23][C:22]2[NH:21][C:20]3[C:19]([C:30]#[N:31])=[CH:18][N:17]=[C:16]([NH:15][CH:12]4[CH2:13][CH2:14][CH:9]([OH:8])[CH:10]([F:32])[CH2:11]4)[C:28]=3[C:27]=2[CH:26]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595431201-[(4-{[tert-Butyl(dimethyl)silyl]oxy}-3-fluorocyclohexyl)amino]-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile

Product 1

HCID 595431238-fluoro-1-[(3-fluoro-4-hydroxycyclohexyl)amino]-5H-pyrido[4,3-b]indole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-[(4-{[tert-butyl(dimethyl)silyl]oxy}-3-fluorocyclohexyl)amino]-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile (135 mg, 0.296 mmol) in THF (4 mL) was added TBAF (1.0 M, 0.89 mL, 0.89 mmol). After the reaction was complete, the reaction was quenched with sodium bicarbonate solution. The mixture was extracted with EtOAc, and the combined organics were dried, concentrated, and purified by prep-HPLC to afford the title compound. LRMS (APCI) calc'd for (C18H16F2N4O) [M+H]+, 343.1. found 343.0.

Workup

  1. customthe reaction was quenched with sodium bicarbonate solution
  2. extractionThe mixture was extracted with EtOAc
  3. customthe combined organics were dried
  4. concentrationconcentrated
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-acdf5b4296654d1dab21d2f9190f09be
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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