Sodium Carbonate → HCID 59526292、化合物

HRID 385720ノート

反応式

HRID 385720 の反応式
Br[C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([C:27]3([OH:31])[CH2:30][O:29][CH2:28]3)=[CH:23][CH:22]=2)O1.C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>C1COCC1.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.CCOC(C)=O>[OH:31][C:27]1([C:24]2[CH:25]=[CH:26][C:21]([C:2]3[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=3)=[CH:22][CH:23]=2)[CH2:30][O:29][CH2:28]1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 534029485-Bromo-2-nitrothiophene-3-carboxamide2 回HCID 583822471093878-29-5

生成物 1

HCID 59526292HCID 59526292、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

5-Bromo-2-nitrothiophene-3-carboxamide (Intermediate 10, Step 4) (1.44 g, 5.74 mmol), 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxetan-3-ol (1.821 g, 6.60 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.331 g, 0.287 mmol) were taken up in THF (25 mL)/2 N Na2CO3 (10 mL) and the reaction mixture was stirred at 80° C. overnight. After cooling to room temperature, saturated NH4Cl and EtOAc were added. The resulting precipitate was collected by filtration, washed with water and dried to give 5-[4-(3-hydroxyoxetan-3-yl)phenyl]-2-nitrothiophene-3-carboxamide as a brown solid (batch 1). The organic phase from the filtrate was separated, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo while loading onto silica. Purification of the residue by flash silica gel column chromatography (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc) gave the title compound as an orange solid after recrystallising from EtOH (batch 2).

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

出典と根拠

ORDレコード
ord-1f209864d480483092592b5c90e3264b
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

読み込み中…