Sodium Carbonate → HCID 135856837、化合物

HRID 1809200ノート

反応式

HRID 1809200 の反応式
Br[C:2]1[N:6]2[CH:7]=[C:8](Br)[N:9]=[C:10]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=2)O1.C([O-])([O-])=O.[Na+].[Na+].[O:46](C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1P(C1C=CC=CC=1)C1C=CC=CC=1>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:46][C:47]1[CH:52]=[CH:51][C:50]([C:2]2[N:6]3[CH:7]=[C:8]([C:32]4[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=4)[N:9]=[C:10]([NH:11][CH2:12][C:13]4[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=4)[C:5]3=[N:4][CH:3]=2)=[CH:49][CH:48]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 25205707HCID 25205707、化合物

生成物 1

HCID 135856837HCID 135856837、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A microwave tube was charged with 4-[(3,6-Dibromo-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide (0.17 g, 0.379 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (0.175 g, 0.79 mmol), Na2CO3 (0.10 g, 0.95 mmol), Pd(OAc)2 (7 mg, 0.028 mmol), and (Oxidi-2,1-phenylene)bis(diphenylphosphine) (20 mg, 0.0379 mmol), suspended in a mixture of DMF (3 mL) and water (1 ml). The tube was sealed under a nitrogen atmosphere then heated to 130° C. for 20 min. The reaction was filtered, diluted with AcOEt and washed with water. The organic layer was dried with MgSO4 anh. filtered and evaporated. The crude mixture was purified by prep. HPLC under acid conditions using a gradient of 0.1% formic acid in H2O/0.1% formic acid in Acetonitrile (95/5:5 min, 9/1:13 min, 0/1:4 min) to give 4-{[3,6-Bis-(4-hydroxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide as a brown solid (21 mg,). LC-MS m/z 488 [M+H]+.

後処理

  1. customThe tube was sealed under a nitrogen atmosphere
  2. filtrationThe reaction was filtered
  3. additiondiluted with AcOEt
  4. washwashed with water
  5. dry with materialThe organic layer was dried with MgSO4 anh. filtered
  6. customevaporated
  7. customThe crude mixture was purified by prep
  8. customa gradient of 0.1% formic acid in H2O/0.1% formic acid in Acetonitrile (95/5:5 min, 9/1:13 min, 0/1:4 min)

出典と根拠

ORDレコード
ord-50cd3ad25ce943a99587b41f27034062
出典データセット
uspto-grants-2013_01
特許番号
US08362018B2

反応ノート

読み込み中…