Tetrabutylammonium Fluoride → (Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one

HRID 20692Notes

Reaction equation

HRID 20692 reaction equation
[Si]([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][O:13][C:14]1[C:15]([O:34][CH3:35])=[CH:16][CH:17]=[C:18]2[C:23]=1[O:22][C:21](=[O:24])[CH:20]=[C:19]2[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=1[Cl:33])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[Cl:33][C:27]1[CH:28]=[N:29][CH:30]=[C:31]([Cl:32])[C:26]=1[NH:25][C:19]1[C:18]2[C:23](=[C:14]([O:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][OH:8])[C:15]([O:34][CH3:35])=[CH:16][CH:17]=2)[O:22][C:21](=[O:24])[CH:20]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86618136HCID 86618136, compound

Product 1

HCID 24849220(Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (Z)-8-(4-(tert-butyldimethylsilyloxy)but-2-enyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one and TBAF (2 mL, 2M THF) was maintained at rt for 18 h, poured into water, and then extracted with EtOAc. The extract was dried, filtered, concentrated, and purified by reverse-phase HPLC (25→100% MeCN/H2O) to give (Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, CD3OD-d6): δ 8.71 (s, 2H), 7.85 (d, 1H), 7.18 (d, 1H), 7.83 (m, 2H), 4.77 (m, 3H), 4.15 (d, 2H), 4.01 (s, 3H); MS (ESI): 422.8.

Workup

  1. extractionextracted with EtOAc
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (25→100% MeCN/H2O)

Sources & evidence

ORD record
ord-ac62aebc72e9427e9373a00eff9e5822
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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