Tetrahydrofuran → 5-Ethyl-2-[2-fluoro-4-(2-hydroxyethylamino)-phenoxy]phenol

HRID 626076Notes

Reaction equation

HRID 626076 reaction equation
C([O:8][C:9]1[CH:26]=[C:25]([CH2:27][CH3:28])[CH:24]=[CH:23][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][OH:21])=[CH:14][C:13]=1[F:22])C1C=CC=CC=1.O1CCCC1>CO>[CH2:27]([C:25]1[CH:24]=[CH:23][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][OH:21])=[CH:14][C:13]=2[F:22])=[C:9]([OH:8])[CH:26]=1)[CH3:28]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 59191271N-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-2-aminoethanol

Product 1

HCID 591912805-Ethyl-2-[2-fluoro-4-(2-hydroxyethylamino)-phenoxy]phenolYield 78.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the procedure of example 20 (b) except substituting 4-ethyl-2-methoxy-1-[4-nitro-2-(trifluoromethyl) phenoxy]benzene for N-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-2-aminoethanol (350 mg, 0.92 mmol) and tetrahydrofurane for methanol (25 mL), the title compound (210 mg; 78%) was obtained as a yellow solid, after purification on silica gel (ethylacetate and petroleum ether: 5/5)

Sources & evidence

ORD record
ord-9a715321dfb14815bc182cf0647c04ce
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

Loading…