4-Methylthiophene-2-boronic acid → HCID 59007070、化合物

HRID 130442

反応式

HRID 130442 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][C@H:22]([CH3:24])[NH:21][C@H:20]([CH3:25])[CH2:19]3)[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:28][C:29]1[CH:30]=[C:31](B(O)O)[S:32][CH:33]=1.CC(C)([O-])C.[K+]>COCCOC.O.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>[CH3:25][C@H:20]1[NH:21][C@@H:22]([CH3:24])[CH2:23][N:18]([C:16]2[CH:15]=[CH:14][C:13]([O:26][CH3:27])=[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([C:31]4[S:32][CH:33]=[C:29]([CH3:28])[CH:30]=4)=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:17]=2)[CH2:19]1

参加物

7

反応物 3

HCID 27343734-Methylthiophene-2-boronic acidHCID 23665647Potassium tert-butoxideHCID 444527764-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

生成物 1

HCID 59007070HCID 59007070、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 4-bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide (E106) (100 mg, 0.22 mmol) and (4-methyl-2-thienyl)boronic acid (71 mg, 0.50 mmol) in DME (3 ml) was added potassium tert-butoxide (220 mg, 1.96 mmol) and tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.01 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. The resulting mixture was then evaporated in vacuo and purified using an SCX cartridge eluting with methanol followed by ammonia (2M in methanol). The appropriate fractions were combined and solvent evaporated in vacuo and the residue purified further by mass directed autoprep HPLC to afford the title compound (E107). MS (ES+) m/e 472 [M+H]+.

後処理

  1. customThe resulting mixture was then evaporated in vacuo
  2. custompurified
  3. washeluting with methanol
  4. customsolvent evaporated in vacuo
  5. customthe residue purified further by mass

出典と根拠

ORDレコード
ord-54c353fc63094d949f46eadf9835d2d8
出典データセット
uspto-grants-2008_06
特許番号
US07381728B2

関連ノート

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