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Sodium Bicarbonate → tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2'-chloro-3'-methyl-3,4'-bipyridine-2-carboxylate

HRID 1778932
ノート
印刷プレビュー

反応式

HRID 1778932 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].C([O-])(O)=O.[Na+].[Cl:50][C:51]1[C:56]([CH3:57])=[C:55](I)[CH:54]=[CH:53][N:52]=1>O1CCOCC1.C(OCC)(=O)C.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>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C:26]([C:55]3[CH:54]=[CH:53][N:52]=[C:51]([Cl:50])[C:56]=3[CH3:57])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]
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 516892Sodium BicarbonateHCID 100836282-Chloro-4-iodo-3-methylpyridineHCID 89498009tert-butyl 6-(8-(benzo[d]thiazol2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate

生成物 1

HCID 89498407tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2'-chloro-3'-methyl-3,4'-bipyridine-2-carboxylate

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a solution of EXAMPLE 30A (1.22 g) in dioxane (4 mL), and aqueous NaHCO3 (2 mL) was added 2-chloro-4-iodo-3-methylpyridine (505 mg), and tetrakis(triphenylphosphine)palladium(0) (115 mg). The mixture was stirred at 120° C. for 20 minutes in a Biotage Initiator microwave reactor. The mixture was diluted with ethyl acetate (300 mL) and washed with water (3 times) and brine, and dried over Na2SO4. Filtration and evaporation of the solvent gave crude product which was loaded on a silica gel column and eluted with 20% ethyl acetate in dichloromethane to provide the title compound.

後処理

  1. washwashed with water (3 times) and brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent
  4. customgave crude product which
  5. washeluted with 20% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-f31554bb1f8a4bd19727e88597d90e1c
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266877B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート