4-Hydroxyphenylboronic acid → Ammonia

HRID 500625Notes

Reaction equation

HRID 500625 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][O:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]([CH3:31])([CH3:30])[CH2:13][CH2:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]#[N:17])[CH2:8]1.[OH:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1>>[NH3:9].[OH:35][C:36]1[CH:41]=[CH:40][C:39]([C:2]2[CH:34]=[CH:33][CH:32]=[C:4]([CH2:5][O:6][C@H:7]3[CH2:11][CH2:10][N:9]([C:12]([CH3:30])([CH3:31])[CH2:13][CH2:14][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:16]#[N:17])[CH2:8]3)[CH:3]=2)=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 59423922HCID 59423922, compound

Product 2

HCID 222AmmoniaHCID 59423912HCID 59423912, compound

Procedure

The title compound was prepared from the product of example 55 and 4-hydroxyphenylboronic acid, using the same method as that described for example 56. The crude compound was purified by column chromatography on silica gel, eluting with ethyl acetate. The appropriate fractions were evaporated under reduced pressure and the residue was further purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 98:2:0.2 to 95:5:0.5, to afford the desired compound as a pale brown gum in 78% yield.

Workup

  1. customThe crude compound was purified by column chromatography on silica gel
  2. washeluting with ethyl acetate
  3. customThe appropriate fractions were evaporated under reduced pressure
  4. customthe residue was further purified by column chromatography on silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-5ef75e93a22b453293a83d7de29fdae6
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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