N-(2-bromobenzyl)acetamide → HCID 86658861, compound

HRID 2194914Notes

Reaction equation

HRID 2194914 reaction equation
[C:1]([O:5][C:6](=[O:46])[NH:7][CH2:8][CH:9]([C:30]1[CH:35]=[CH:34][C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][C:31]=1[CH3:45])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:48]1[CH:58]=[CH:57][CH:56]=[CH:55][C:49]=1[CH2:50][NH:51][C:52](=[O:54])[CH3:53]>>[C:52]([NH:51][CH2:50][C:49]1[CH:55]=[CH:56][CH:57]=[CH:58][C:48]=1[C:33]1[CH:34]=[CH:35][C:30]([CH:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:22]([Cl:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=3[Cl:27])=[CH:13][CH:12]=2)[CH2:8][NH:7][C:6](=[O:46])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[C:31]([CH3:45])[CH:32]=1)(=[O:54])[CH3:53]

Participants

3

Reactant 2

HCID 2824953N-(2-bromobenzyl)acetamideHCID 86658858HCID 86658858, compound

Product 1

HCID 86658861HCID 86658861, compound

Procedure

Prepared according to the procedure described in EXAMPLE 7, step 2 using tert-butyl{3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl}carbamate from EXAMPLE 9, step 1 and N-(2-bromobenzyl)acetamide (V.13) as starting materials. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 100% in 15 min) afforded the desired compound as a colorless oil.

Workup

  1. customPrepared
  2. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  3. washeluting with Hex/EtOAc (10 to 100% in 15 min)

Sources & evidence

ORD record
ord-c499889661d44c97b1c56e0df763126c
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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