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Cesium carbonate → 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

HRID 716030
ノート
印刷プレビュー

反応式

HRID 716030 の反応式
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[OH:33][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]3=[N:6][CH:7]=2)=[CH:27][CH:28]=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 3

HCID 10796Cesium carbonateHCID 693314-Aminobenzyl alcoholHCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one

生成物 1

HCID 710153161-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one収率 215.4%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 634876Binap, (A+-)-触媒
HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a 35 ml sealed tube, 1-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one (2.0 g, 0.0048 mole) and (4-aminophenyl)methanol (0.78 g, 0.0063 mole) was taken in toluene (20.0 ml). The reaction mixture was purged with argon for 15 min at RT followed by Cs2CO3 (4.7 g, 0.0144 mole) was added and further purged for 30 min with argon. BINAP (0.06 g, 0.0001 mole) and Pd(OAc)2 (0.021 g, 0.0001 mole) were added to reaction mixture and heated to 110° C. for 4 hr. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with ethyl acetate. Filtrate was collected and concentrated to afford crude product which was subjected for the column purification. The reaction with repeated twice and the crude product from each reaction was mixed and then purified using column purification by eluting the compound with 25-30% ethyl acetate in hexanes to yield 4.7 g of 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one.

後処理

  1. customTo a 35 ml sealed tube
  2. customThe reaction mixture was purged with argon for 15 min at RT
  3. additionwas added
  4. customfurther purged for 30 min with argon
  5. customAfter completion of the reaction
  6. filtrationthe reaction mixture was filtered through celite bed
  7. washwashed with ethyl acetate
  8. customFiltrate was collected
  9. concentrationconcentrated
  10. customto afford crude product which
  11. customwas subjected for the column purification
  12. customThe reaction
  13. custompurified
  14. customcolumn purification
  15. washby eluting the compound with 25-30% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-44c5969376e24a048035e85f1ceb0000
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187487B2

反応ノート

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