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2-Methyl-2-butanol → 2-({6-[(2-Hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)-5-[4-(methylsulfonyl)phenyl]thiophene-3-carboxamide

HRID 385850
ノート
印刷プレビュー

反応式

HRID 385850 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].Br[C:21]1[N:26]=[C:25]([CH2:27][O:28][CH2:29][C:30]([CH3:33])([OH:32])[CH3:31])[CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(O)(CC)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:32][C:30]([CH3:33])([CH3:31])[CH2:29][O:28][CH2:27][C:25]1[N:26]=[C:21]([NH:1][C:2]2[S:3][C:4]([C:10]3[CH:11]=[CH:12][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][CH:15]=3)=[CH:5][C:6]=2[C:7]([NH2:9])=[O:8])[CH:22]=[CH:23][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 64052-Methyl-2-butanolHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 582564812-Amino-5-[4-(methylsulfonyl)phenyl]thiophene-3-carboxamideHCID 583352721-[(6-Bromopyridin-2-yl)methoxy]-2-methylpropan-2-ol

生成物 1

HCID 59525722
2-({6-[(2-Hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)-5-[4-(methylsulfonyl)phenyl]thiophene-3-carboxamide

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

2-Amino-5-[4-(methylsulfonyl)phenyl]thiophene-3-carboxamide (150 mg, 0.51 mmol), 1-[(6-bromopyridin-2-yl)methoxy]-2-methylpropan-2-ol (Example 217 Step 1) (125 mg, 0.48 mmol), Pd2 dba3 (46.3 mg, 0.051 mmol), K2CO3 (77 mg, 0.557 mmol) and X-Phos (120 mg, 0.25 mmol) were added to a 5 mL microwave vial. Degassed tert-amyl alcohol (1.2 mL) was added and the vial evacuated and back-filled with N2 (3×). The resulting mixture was stirred at 100° C. overnight. After cooling to room temperature, the mixture was diluted with methanol, silica gel was added, and the solvent was removed in vacuo. Purification of the residue by flash chromatography (silica, 0-10% MeOH-DCM) gave the title compound as a yellow solid.

後処理

  1. customthe vial evacuated
  2. additionback-filled with N2 (3×)
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with methanol, silica gel
  5. additionwas added
  6. customthe solvent was removed in vacuo
  7. customPurification of the residue by flash chromatography (silica, 0-10% MeOH-DCM)

出典と根拠

ORDレコード
ord-4046905124d546f29a50d2208ae64d3a
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367706B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート