HCID 58488450, compound → HCID 86658862, compound

HRID 2194916Notes

Reaction equation

HRID 2194916 reaction equation
[Cl:1][C:2]1[CH:44]=[C:43]([CH3:45])[CH:42]=[C:41]([Cl:46])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:26]=2[CH3:40])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:10][CH:9]=1.Br[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH2:54][CH2:55][CH2:56][NH:57][C:58](=[O:60])[CH3:59]>>[C:58]([NH:57][CH2:56][CH2:55][CH2:54][C:49]1[CH:48]=[CH:53][CH:52]=[CH:51][C:50]=1[C:28]1[CH:29]=[CH:30][C:25]([CH:15]([CH2:14][C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][O:4][C:3]3[C:2]([Cl:1])=[CH:44][C:43]([CH3:45])=[CH:42][C:41]=3[Cl:46])=[CH:13][CH:12]=2)[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[C:26]([CH3:40])[CH:27]=1)(=[O:60])[CH3:59]

Participants

3

Reactant 2

HCID 58488450HCID 58488450, compoundHCID 86658858HCID 86658858, compound

Product 1

HCID 86658862HCID 86658862, 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-[3-(2-bromophenyl)propyl]acetamide (V.15) 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-83e71c751b40419e811339f4925860d3
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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