Nitrogen → HCID 118022266、化合物

HRID 518292ノート

反応式

HRID 518292 の反応式
N#N.Br[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[N:6]([CH3:15])[CH:5]=1.[CH3:16][N:17]1[CH:21]=[C:20](B(O)O)[CH:19]=[N:18]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:15][N:6]1[CH:5]=[C:4]([C:20]2[CH:19]=[N:18][N:17]([CH3:16])[CH:21]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:14]

参加物

7

反応物 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 3118584-Bromo-2-methylisoquinolin-1(2H)-oneHCID 112635011-Methyl-1H-pyrazole-4-boronic acid

生成物 1

HCID 118022266HCID 118022266、化合物収率 52.2%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

実験手順

For 3 min, N2 was bubbled through a mixture of 4-bromo-2-methylisoquinolin-1(2H)-one (54 mg, 0.23 mmol), (1-methylpyrazol-4-yl)boronic acid (31 mg, 0.25 mmol), aqueous 2M Na2CO3 (0.375 mL) and Pd(dppf)Cl2 (8 mg, 0.01 mmol) in 1,4-dioxane (1.5 mL) which was then microwaved at 120° C. for 1 h. Work up in a manner similar to Example 18, step 3, and two successive silica gel chromatographies, eluting with 15-80% EA in hexane over 6 min and continuing 80% isocratic EA followed by a second chromatography 15-100% EA in hexane over 6 min and continuing 100% isocratic EA gave the title compound (28 mg, 0.12 mmol) as a cream solid in 51% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.54 (s, 3H) 3.92 (s, 3H) 7.50 (s, 1H) 7.55 (ddd, J=8.02, 5.87, 2.27 Hz, 1H) 7.60-7.64 (m, 1H) 7.70-7.80 (m, 2H) 7.95 (s, 1H) 8.31 (d, J=7.83 Hz, 1H). LCMS (M+H)+ 240.

後処理

  1. customwas then microwaved at 120° C. for 1 h
  2. washeluting with 15-80% EA in hexane over 6 min
  3. waitfollowed by a second chromatography 15-100% EA in hexane over 6 min

出典と根拠

ORDレコード
ord-1fe3360fa6db41449216b3096f108915
出典データセット
uspto-grants-2015_08
特許番号
US09115114B2

反応ノート

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