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Cesium carbonate → HCID 56953390、化合物

HRID 2366187
ノート
印刷プレビュー

反応式

HRID 2366187 の反応式
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([C:26]#[N:27])[CH:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH:19][C:20]3[N:25]=[CH:24][N:23]=[C:22]([C:26]#[N:27])[CH:21]=3)=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 668018016-Aminopyrimidine-4-carbonitrileHCID 862804124-Bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine

生成物 1

HCID 56953390HCID 56953390、化合物収率 35%

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 312751,4-Dioxane溶媒

実験手順

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (60 mg, 0.17 mmol), 6-aminopyrimidine-4-carbonitrile (0.029 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos (0.017 g, 0.034 mmol) and Cs2CO3 (0.11 g, 0.34 mmol) in dioxane (3.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160° C. for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified with reverse phase column chromatography, eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a white solid (21 mg, 35% yield). 1H NMR (500 MHz, DMSO-d6): δ 11.43 (s, 1H), 8.91 (s, 1H), 8.54 (d, J=5.0 Hz, 1H), 8.31 (s, 1H), 8.00 (d, J=5.0 Hz, 1H), 7.76-7.67 (m, 3H). LCMS (Method B): RT=6.30 min, m/z: 399.0 [M+H+].

後処理

  1. customThe mixture was degassed with N2 for 10 minutes
  2. customirradiated in a microwave reactor at 160° C. for 2 hours
  3. customwas removed via filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified with reverse phase column chromatography
  6. washeluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3

出典と根拠

ORDレコード
ord-8cbbf2a9ef254b2499f9b11e8a98fb0c
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08697708B2

反応ノート

読み込み中…

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