Tetrabutylammonium Fluoride → HCID 11795219, compound

HRID 2228550Notes

Reaction equation

HRID 2228550 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[C:6]([NH:8][C:9]1[C:10]([NH:23][C:24](=[O:34])[C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:11][C:12]([O:15][Si](C)(C)C(C)(C)C)=[CH:13][CH:14]=1)=[O:7])#[N:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[C:6]([NH:8][C:9]1[C:10]([NH:23][C:24](=[O:34])[C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10529800HCID 10529800, compound

Product 1

HCID 11795219HCID 11795219, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N1-(3-cyanobenzoyl)-N2-(4-isopropylbenzoyl)-4-(dimethyl-t-butylsiloxy)-1,2-benzenediamine (1.57 g, 3.05 mmol) THF (30 mL) at 0° C. was added a THF solution of TBAF (3.1 mL, 3.1 mmol). After 1 h, the reaction was quenched with water (35 mL) and extracted with ether (2×200 mL). The combined organic layers was MgSO4 dried, filtered, and concentrated. The residue was chromatographed (1:1 EtOAc/hexanes) to give the title compound as a solid (1.10 g, 91%); IR(KBr): 3277, 1629, 1600, 1535, 1478, 1299 cm−1; NMR(300 MHz, d6-DMSO): δ10.02 (s, 1H), 9.70 (s, 1H), 9.56 (s, 1H), 8.31 (s, 1H), 8.18 (d, J=7.5, 1H), 8.01 (d, J=7.2, 1H), 7.79 (d, J=8.1, 2H), 7.70 (m, 1H), 7.34-7.21 (m, 4H), 6.63 (d, J=9.0, 1H), 2.90 (m, 1H), 1.17 (s, 3H), 1.15 (s, 3H); MS(FD): 399.1.

Workup

  1. customthe reaction was quenched with water (35 mL)
  2. extractionextracted with ether (2×200 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed (1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-2ca5357a63864bb0962b581d1e09909e
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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