Sodium Bicarbonate → 5-{[4-(2-Azepan-1-yl-ethoxy)-phenyl]-hydroxymethyl}-6-(2,5-difluorophenyl)-naphthalen-2-ol

HRID 1513963Notes

Reaction equation

HRID 1513963 reaction equation
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[F:37])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([BH-](CC)CC)C.[Li+].C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl.C(O)(C)C>C1COCC1>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([OH:18])[C:19]3[C:20]([C:30]4[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=4[F:37])=[CH:21][CH:22]=[C:23]4[C:28]=3[CH:27]=[CH:26][C:25]([OH:29])=[CH:24]4)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 21906603Chloroform isopropyl alcoholHCID 23664628Lithiumtriethylborohydride2×HCID 67004614[4-(2-Azepan-1-yl-ethoxy)-phenyl][2-(2,5-difluorophenyl)-6-hydroxynaphthalen-1-yl]-methanone

Product 1

HCID 670045865-{[4-(2-Azepan-1-yl-ethoxy)-phenyl]-hydroxymethyl}-6-(2,5-difluorophenyl)-naphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve [4-(2-azepan-1-yl-ethoxy)-phenyl]-[2-(2,5-difluorophenyl)-6-hydroxynaphthalen-1-yl]-methanone (770 mg, 1.54 mmol) in 10 mL THF and add 5.0 mL (5.0 mmol) of lithium triethylborohydride (1.0 M solution in THF). After one hour at room temp, add another 4.0 mL of the lithium triethylborohydride gently warm the solution with a heat gun. After ½ hour the reaction is complete. Quench the reaction with water and pour into a two phase system of saturated sodium bicarbonate and a 3/1 mixture of chloroform/isopropanol. Separate the phases, dry the organic layer with 3 Å sieves and evaporate to give the title compound to be taken on to the next step without purification.

Workup

  1. temperaturegently warm the solution with a heat gun
  2. waitAfter ½ hour the reaction is complete
  3. customQuench
  4. customthe reaction with water
  5. customSeparate the phases
  6. customdry the organic layer with 3 Å sieves
  7. customevaporate

Sources & evidence

ORD record
ord-1c29d9326efb485ca67a719a56a4501a
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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