Tetrabutylammonium Fluoride → HCID 86670548, compound

HRID 874715Notes

Reaction equation

HRID 874715 reaction equation
[NH2:1][C:2]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]3)=[CH:14][CH:13]=2)([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]#[C:26][Si](C)(C)C)[CH:8]=2)[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:1][C:2]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]3)=[CH:14][CH:13]=2)([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]#[CH:26])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67167406HCID 67167406, compound

Product 1

HCID 86670548HCID 86670548, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-amino-3-{4-[3-(trifluoromethyl)diazirin-3-yl]phenyl}-5-[2-(trimethylsilyl)ethynyl]indol-3-ol (30.5 mg, 0.07 mmol, 1 eq.) was dissolved in THF (5 mL), and 1 M TBAF in THF (0.078 mL, 0.08 mmol, 1.1 eq.) was added. The reaction was stirred at room temperature for 10 minutes. Solvents were then evaporated, and the residue was purified by silica column (DCM/MeOH, 39:1→19:1→9:1→4:1), resulting in 21.8 mg (86%) of the title compound as a yellow solid. 1H NMR (500 MHz, CD3OD) δ 7.45 (d, J=8.5, 2H, Ar—H), 7.33 (dd, J=1.5, 8.0, 1H, Ar—H), 7.23 (d, J=8.2, 2H, Ar—H), 7.10-6.94 (m, 2H, Ar—H). 13C NMR (126 MHz, CD3OD) δ 180.61 (CNH2), 156.96 (C—Ar), 144.65 (C—Ar), 140.97 (C—Ar), 135.30 (C—Ar), 129.59 (C—Ar), 127.92 (d, J=0.90, C—Ar), 127.76 (C—Ar), 127.02 (C—Ar), 123.73 (q, J=273.90, CF3), 117.13 (C—Ar), 116.69 (C—Ar), 84.96 (CCH), 84.23 (Ar—COH), 77.31 (CCH), 29.56 (q, J=40.35, CN2). Exact Mass, 356.09. 354.7202 [M−H]−, 356.7268 [M+H]+.

Workup

  1. customSolvents were then evaporated
  2. customthe residue was purified by silica column (DCM/MeOH, 39:1→19:1→9:1→4:1)

Sources & evidence

ORD record
ord-ac78428e0f6f45f586177a4cb9f04ac3
Source dataset
uspto-grants-2015_03
Patent number
US08980926B2

Reaction notes

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