Lithium Chloride → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(4-chloropyrimidin-2-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

HRID 879515ノート

反応式

HRID 879515 の反応式
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[Cl-].[Li+].C([Sn](CCCC)(CCCC)[C:37]1[N:42]=[C:41]([Cl:43])[CH:40]=[CH:39][N:38]=1)CCC>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.[Cu]I>[C:25]([O:24][C@@H:18]([C:9]1[C:8]([CH3:29])=[CH:7][C:5]2[N:6]=[C:2]([C:37]3[N:42]=[C:41]([Cl:43])[CH:40]=[CH:39][N:38]=3)[S:3][C:4]=2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:28])([CH3:27])[CH3:26]

参加物

7

反応物 3

HCID 433294Lithium ChlorideHCID 149763044-Chloro-2-(tributylstannyl)pyrimidineHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

生成物 1

HCID 86700335(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(4-chloropyrimidin-2-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (500 mg, 1.01 mmol), tetrakis(triphenylphosphine)palladium(0) (174 mg, 0.15 mmol), lithium chloride (128 mg, 3.02 mmol), and copper(I) iodide (58 mg, 0.3 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added 2-(tributylstannyl)-4-chloropyrimidine (447 mg, 1.11 mmol) in dioxane (12 mL) and the resulting mixture was stirred at 90° C. for 18 h. The reaction mixture was then cooled, filtered through Celite (ethyl acetate eluent), and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+ calc'd for C26H26Cl2N3O3S (M+H+): 530.1; Found: 530.0 (M+H+).

後処理

  1. customflushed with argon three times
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered through Celite (ethyl acetate eluent)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
  6. customprovided the product

出典と根拠

ORDレコード
ord-c357c7caa6fd4aa9b14d3d6ea46f4f78
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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