Potassium Carbonate → N-[3-[3,5-Bis(methyloxy)phenyl]-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide

HRID 573677ノート

反応式

HRID 573677 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:22])=[CH:8][C:9]=2[NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)(=[O:14])=[O:13])[S:4][C:3]=1[C:23]1[CH:24]=[N:25][N:26](C(OC(C)(C)C)=O)[CH:27]=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:40]=[C:41]([O:43][CH3:44])[CH:42]=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.O.CN(C=O)C>[CH3:35][O:36][C:37]1[CH:38]=[C:39]([C:2]2[C:10]3[C:5](=[N:6][C:7]([CH3:22])=[CH:8][C:9]=3[NH:11][S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)(=[O:13])=[O:14])[S:4][C:3]=2[C:23]2[CH:27]=[N:26][NH:25][CH:24]=2)[CH:40]=[C:41]([O:43][CH3:44])[CH:42]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 162176602-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 683240291,1-Dimethylethyl 4-(3-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridin-2-yl)-1H-pyrazole-1-carboxylate

生成物 1

HCID 68380771N-[3-[3,5-Bis(methyloxy)phenyl]-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide収率 48.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 1,1-dimethylethyl 4-(3-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridin-2-yl)-1H-pyrazole-1-carboxylate (Description 75) (100 mg, 0.171 mmol), 3,5-dimethoxyphenylboronic acid pinacol ester (90 mg, 0.343 mmol), potassium carbonate (95 mg, 0.685 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.96 mg, 3.43 μmol) were weighed into a microwave vial. 1,4-Dioxane (1.5 mL), DMF (0.75 mL) and water (0.38 mL) were added and the mixture heated in a microwave at 110° C. for 30 min. At this point, both reaction mixtures were combined and concentrated. The residue was passed through an SCX cartridge, eluting with MeOH (75 mL) and then with 2M NH3 in MeOH (100 mL). The basic methanolic solution was concentrated and purified by MDAP (acidic conditions), to give the title compound (45 mg). LCMS (A) m/z: 541 [M+1]+, Rt 1.26 min (acidic).

後処理

  1. customAt this point, both reaction mixtures
  2. concentrationconcentrated
  3. washeluting with MeOH (75 mL)
  4. concentrationThe basic methanolic solution was concentrated
  5. custompurified by MDAP (acidic conditions)

出典と根拠

ORDレコード
ord-e8ff783883794fbbb1ba79c2cfd444c2
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

読み込み中…