4-Hydroxyphenylboronic acid → Ammonia

HRID 2387683Notes

Reaction equation

HRID 2387683 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-468ba288043d40dab67ab2c68055f0ef
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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