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 2194901ノート

反応式

HRID 2194901 の反応式
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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4d23e93d73854215a67c44ef0142da61
出典データセット
uspto-grants-2012_12
特許番号
US08334308B2

反応ノート

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