Toluene → HCID 59007076、化合物

HRID 130453

反応式

HRID 130453 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.[S:28]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29]1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>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:30]4[CH:31]=[CH:32][S:28][CH:29]=4)=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:17]=2)[CH2:19]1

参加物

8

反応物 4

HCID 1140TolueneHCID 581760Thiophene-3-boronic acidHCID 23665647Potassium tert-butoxideHCID 444527764-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

生成物 1

HCID 59007076HCID 59007076、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) (200 mg, 0.44 mmol) and 3-thienylboronic acid (113 mg, 0.88 mmol) in DME (3 ml) was added potassium tert-butoxide (445 mg, 3.97 mmol) and tetrakis(triphenylphosphine)palladium(0) (30.5 mg, 0.03 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. 2-3 ml of toluene added and solvent evaporated, the residue dissolved in methanol and added to a preconditioned (methanol) SCX cartridge eluting with methanol (×3), ammonia (1M in methanol (×2)) and then ammonia (2M in methanol (×3)), followed by by mass directed autoprep HPLC followed by trituration with diethyl ether to afford the title compound (E119). MS (AP+) m/e 458 [M+H]+.

後処理

  1. customsolvent evaporated
  2. dissolutionthe residue dissolved in methanol
  3. additionadded to a preconditioned (methanol) SCX cartridge
  4. washeluting with methanol (×3), ammonia (1M in methanol (×2))

出典と根拠

ORDレコード
ord-6fa43e0a7b12449981c07cd9a18b8e8e
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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