Tetrabutylammonium Fluoride → HCID 19608776, compound

HRID 1603046Notes

Reaction equation

HRID 1603046 reaction equation
[Si]([O:8][CH2:9][CH:10]([NH:20][C:21]([C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[C:28]([C:32]([O:34][CH3:35])=[O:33])[NH:29]2)=[CH:25][CH:24]=1)=[O:22])[CH2:11][O:12][Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH:10]([NH:20][C:21]([C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[C:28]([C:32]([O:34][CH3:35])=[O:33])[NH:29]2)=[CH:25][CH:24]=1)=[O:22])[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19608785HCID 19608785, compound

Product 1

HCID 19608776HCID 19608776, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[1,3-bis(t-butyldimethylsilyloxy)-2-propyl]-2-(methoxycarbonyl)indole-6-carboxamide (744 mg, 1.43 mmol) and tetrabutylammonium fluoride (2.9 mL of a 1M solution in THF, 2.9 mmol) in THF (20 mL) was stirred at 20° C. for 80 min and evaporated. The residue was crystallised from MeOH (10 mL) giving N-(1,3-dihydroxy-2-propyl)-2-(methoxycarbonyl)indole-6-carboxamide as a white solid (305 mg, 73%), mp 205-207° C. Dry column chromatography of the mother liquor (eluting with 20:1 EtOAc:MeOH) gave a second crop (57 mg, 14%). 1H NMR [(CD3)2SO] δ12.22 (s, 1H, indole NH), 7.97 (s, 1H, H-3 or H-7), 7.94 (d, J=8.0 Hz, 1H, amide NH), 7.70 (d, J=8.5 Hz, 1H, H-4), 7.59 (dd, J=8.5, 1.3 Hz, 1H, H-5), 7.20 (d, J=1.6 Hz, 1H, H-3 or H-7), 4.66 (t, J=5.7 Hz, 2H, OH), 4.03-3.95 (m, 1H, CONHCH), 3.90 (s, 3H, CO2Me), 3.54 (t, J=5.8 Hz, 4H, CH2OH). Anal. (C14H16N2O5) C,H,N.

Workup

  1. customevaporated
  2. customThe residue was crystallised from MeOH (10 mL)

Sources & evidence

ORD record
ord-b7077cbf4264453db34dca16cdb1d5dc
Source dataset
uspto-grants-1999_11
Patent number
US05985909

Reaction notes

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