Tetrahydrofuran → HCID 86603019, compound

HRID 735455Notes

Reaction equation

HRID 735455 reaction equation
FC1C=C[C:5]([NH:8]C(=O)OC)=[C:4]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:22]([CH2:34][C:35]4[C:40]([F:41])=[CH:39][C:38]([F:42])=[CH:37][C:36]=4[F:43])[N:23]=[C:24]4[C:29]=3[CH:28]=[CH:27][CH:26]=[C:25]4[C:30]([F:33])([F:32])[F:31])[CH:16]=2)C=1.[F-:44].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:62]1[CH2:66]O[CH2:64][CH2:63]1>>[F:44][C:63]1[CH:64]=[C:4]2[C:5](=[CH:66][CH:62]=1)[NH:8][C:14]([C:15]1[CH:16]=[C:17]([C:21]3[N:22]([CH2:34][C:35]4[C:40]([F:41])=[CH:39][C:38]([F:42])=[CH:37][C:36]=4[F:43])[N:23]=[C:24]4[C:29]=3[CH:28]=[CH:27][CH:26]=[C:25]4[C:30]([F:32])([F:33])[F:31])[CH:18]=[CH:19][CH:20]=1)=[CH:13]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86603020HCID 86603020, compound

Product 1

HCID 86603019HCID 86603019, compound

Procedure

A solution of methyl [4-fluoro-2-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}ethynyl)phenyl]carbamate (0.07 g, 0.12 mmol) and tetrabutylammonium fluoride (0.24 mL, 0.24 mmol, 1M solution in THF) in 2 mL THF was heated at 60° C. for 21 hours. The reaction mixture was concentrated in vacuo and the residue purified by normal phase HPLC (silica, hexane-EtOAC, 19:1) to give 0.045 g of product as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by normal phase HPLC (silica, hexane-EtOAC, 19:1)

Sources & evidence

ORD record
ord-a50827c807664b789f95997f3bd5f073
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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