Potassium Carbonate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(2-chloropyridin-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

HRID 510275ノート

反応式

HRID 510275 の反応式
[C:1]([O:7][CH2:8][C@@H:9]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:46][C:47]1[CH:52]=[C:51](B(O)O)[CH:50]=[CH:49][N:48]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:7][CH2:8][C@@H:9]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])[C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:51]4[CH:50]=[CH:49][N:48]=[C:47]([Cl:46])[CH:52]=4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)(=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 86699797(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy)phenyl)benzo[d]thiazol-6-yl)ethyl pivalate

生成物 1

HCID 86699806(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(2-chloropyridin-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

The reaction mixture of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy)phenyl)benzo[d]thiazol-6-yl)ethyl pivalate (30 mg, 0.0438 mmol), 2-chloropyridine-4-boronic acid (10 mg, 0.0657 mmol), 2N K2CO3 (100 μL), Pd(PPh3)4 (5.0 mg, 0.0044 mmol) in dioxane (2 mL) was heated at 120° C. in sealed tube for 2 hs. The reaction was washed by sat. NaHCO3, extracted by EtOAc, dried by MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product (LCMS-ESI+: calc'd for C36H36Cl2N2O3S: 647.2 (M+H+); Found: 647.3 (M+H+).

後処理

  1. washThe reaction was washed by sat. NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialdried by MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down
  6. custompurified by silica gel column
  7. washeluting by 0-100% EtOAc in hexanes
  8. customto give the product (LCMS-ESI+: calc'd for C36H36Cl2N2O3S

出典と根拠

ORDレコード
ord-637da953ac304717ba6126bac369f5cb
出典データセット
uspto-grants-2015_08
特許番号
US09096586B2

反応ノート

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