Water → HCID 86699734, compound

HRID 515163Notes

Reaction equation

HRID 515163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2[O:24]C)=[CH:4][CH:3]=1.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[OH:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 72187884HCID 72187884, compound

Product 1

HCID 86699734HCID 86699734, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(4-chlorophenyl)-methyl]-2-methoxy-6-methyl-4-morpholin-4-yl-benzamide (synthesized according to the methods described in sections a) to f) of example 10) (0.25 g, 0.67 mmol) in dichloromethane (10 ml) is added neat boron tribromide (0.095 ml, 1.0 mmol) at −78° C. The temperature is slowly raised to RT over a period of 30 min and stirred for 1 h at RT. The reaction mixture is poured onto cold water and extracted with dichloromethane (3×30 ml). The combined organic layers are washed with brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude material is purified by column chromatography (silica gel, 40% ethyl acetate/hexane) affording N-[(4-chlorophenyl)-methyl]-2-hydroxy-6-methyl-4-morpholin-4-yl-benzamide (0.11 g, 0.30 mmol, 45%).

Workup

  1. extractionextracted with dichloromethane (3×30 ml)
  2. washThe combined organic layers are washed with brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude material is purified by column chromatography (silica gel, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-615ce37c531c4385a1ecab63029ae617
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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