(5-Chloro-2-methoxypyridin-4-yl)boronic acid → 6-(5-Chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole

HRID 1944677

反応式

HRID 1944677 の反応式
Br[C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH:15]4[CH2:17][CH2:16]4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.B(O)(O)[C:21]1[C:26]([Cl:27])=[CH:25][N:24]=[C:23]([O:28][CH3:29])[CH:22]=1.CC(O[K])=O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:27][C:26]1[C:21]([C:2]2[CH:19]=[CH:18][C:5]3[N:6]=[C:7]([N:9]4[CH2:14][CH2:13][N:12]([CH:15]5[CH2:17][CH2:16]5)[CH2:11][CH2:10]4)[S:8][C:4]=3[CH:3]=2)=[CH:22][C:23]([O:28][CH3:29])=[N:24][CH:25]=1

参加物

6

反応物 3

HCID 11030558(5-Chloro-2-methoxypyridin-4-yl)boronic acidHCID 595888036-Bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazoleHCID 178476685HCID 178476685、化合物

生成物 1

HCID 237288926-(5-Chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole収率 6%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 6-bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (500 mg, 1.48 mmol) and 5-chloro-2-methoxypyridin-4-yl-4-boronic acid (334 mg, 1.78 mmol) in DMF (20 mL) was added PdCl2(dppf) (108 mg, 0.148 mmol), followed by CH3COOK (581 mg, 5.92 mmol). The mixture was heated at 80° C. for 2 h, filtered and the volatiles evaporated. Water (5 mL) was added and the mixture was extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by the preparative HPLC to give 35 mg (6%) of 6-(5-chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole as a trifluoroacetate salt.

後処理

  1. filtrationfiltered
  2. customthe volatiles evaporated
  3. additionWater (5 mL) was added
  4. extractionthe mixture was extracted with CH2Cl2 (3×5 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by the preparative HPLC

出典と根拠

ORDレコード
ord-f527a6e539aa43ec8b9cc303bf4025d2
出典データセット
uspto-grants-2013_03
特許番号
US08394842B2

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