Tetrabutylammonium Fluoride → HCID 10172946, compound

HRID 1376151Notes

Reaction equation

HRID 1376151 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][CH2:29][N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH:32]([NH:40][C:41]([C:43]2[NH:44][C:45]3[C:50]([CH:51]=2)=[CH:49][C:48]([Cl:52])=[CH:47][CH:46]=3)=[O:42])[C:31]1=[O:53])(C(C)(C)C)(C)C>C1COCC1>[Cl:52][C:48]1[CH:49]=[C:50]2[C:45](=[CH:46][CH:47]=1)[NH:44][C:43]([C:41]([NH:40][CH:32]1[CH2:33][C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:30]([CH2:29][CH2:28][CH2:27][OH:26])[C:31]1=[O:53])=[O:42])=[CH:51]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58788451HCID 58788451, compound

Product 1

HCID 10172946HCID 10172946, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of TBAF in THF (1 mL) was added dropwise to a solution of N-[1-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-5-chloro-1H-indole-2-carboxamide (Method 13, 400 mg, 0.78 mmol) in THF (5 mL). The reaction was stirred at ambient temperature for 24 h, partitioned between EtOAc (25 mL) and saturated aqueous NH4Cl solution (20 mL), the layers separated and the organic phase dried (MgSO4). The volatiles were removed under reduced pressure to give an off-white solid which was washed with water, isohexane, diethyl ether and dried under vacuum to give the title compound (234 mg, 75%) as an off-white solid.

Workup

  1. custompartitioned between EtOAc (25 mL) and saturated aqueous NH4Cl solution (20 mL)
  2. customthe layers separated
  3. dry with materialthe organic phase dried (MgSO4)
  4. customThe volatiles were removed under reduced pressure
  5. customto give an off-white solid which
  6. washwas washed with water, isohexane, diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-bc454c6570a94e6fbc215ea118f59090
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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