Barium hydroxide → Tert-butyl{3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(3-methoxypropyl)-3,6'-dimethylbiphenyl-4-yl]propyl}carbamate

HRID 2194901노트

반응식

HRID 2194901 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]3[C:34]([Cl:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=3[Cl:37])=[CH:21][CH:20]=2)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([CH3:38])[CH:3]=1.[CH3:39][O:40][CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:50])[C:45]=1B(O)O.C(COC)OC.O.[OH-].[Ba+2].[OH-]>O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:13]([O:12][C:11](=[O:17])[NH:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:45]2[C:46]([CH3:50])=[CH:47][CH:48]=[CH:49][C:44]=2[CH2:43][CH2:42][CH2:41][O:40][CH3:39])=[CH:3][C:4]=1[CH3:38])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]2[C:30]([Cl:37])=[CH:31][C:32]([CH3:36])=[CH:33][C:34]=2[Cl:35])=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]

참가 물질

7

반응물 4

HCID 6093286Barium hydroxideHCID 18180031Water 1,2-dimethoxyethaneHCID 58083342[2-(3-Methoxypropyl)-6-methylphenyl]boronic acidHCID 86658849Tert-butyl (2-(4-bromo-2-methylphenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propyl)carbamate

생성물 1

HCID 131730111Tert-butyl{3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(3-methoxypropyl)-3,6'-dimethylbiphenyl-4-yl]propyl}carbamate

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

실험 절차

To a solution tert-butyl (2-(4-bromo-2-methylphenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propyl)carbamate from EXAMPLE 2, step 2 (1 eq.) and [2-(3-methoxypropyl)-6-methylphenyl]boronic acid from step 1 (1.1 eq.) in 1-2 dimethoxyethane/water (6/1; 0.1M) at room temperature was added palladium tetrakis(triphenylphosphine) (0.05 eq.) and Barium hydroxide (1.5 eq.). The mixture was stiffed at 80° C. for 5 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 70%, in 30 min) afforded the desired compound.

후처리

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  8. washeluting with Hex/EtOAc (10 to 70%, in 30 min)

출처 및 근거

ORD 기록
ord-4d23e93d73854215a67c44ef0142da61
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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