Sodium Carbonate → HCID 86715474、化合物

HRID 2284566

反応式

HRID 2284566 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[CH:5]2.[Cl:12][C:13]1[C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+].ClC1C(C2C=C3C(=CC=2)NN=C3)=CC=CN=1>O1CCOCC1.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>[Cl:12][C:13]1[C:18]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH3:11])[N:6]=[CH:5]3)=[CH:17][CH:16]=[CH:15][N:14]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 120670602-Chloropyridine-3-boronic acid pinacol esterHCID 225587255-Bromo-1-methyl-1H-indazoleHCID 867154695-(2-chloropyridin-3-yl)-1H-indazole

生成物 1

HCID 86715474HCID 86715474、化合物収率 73.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

Analogous to the preparation of 5-(2-chloropyridin-3-yl)-1H-indazole,5-(2-chloropyridin-3-yl)-1-methyl-1H-indazole was prepared by heating the mixture of 5-bromo-1-methyl-1H-indazole (1.0 g, 4.7 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (1.2 g, 5.2 mmol), Pd(PPh3)4 (270 mg, 0.23 mmol) and 2M aq. Na2CO3 (6 mL, 12 mmol) in 1,4-dioxane (75 mL) under argon atmosphere for 12 h. Upon work-up as discussed in the preparation of 5-(2-chloropyridin-3-yl)-1H-indazole and purification of the concentrate by flash silica gel column chromatography [Combiflash® companion System® with RediSep® silica gel column 40 g, 30-50% EtOAc/hexanes eluting solvent gradient upon dry loading the concentrate absorbed on silica gel] provided 5-(2-chloropyridin-3-yl)-1methyl-1H-indazole as white solid (0.84 g, 73%). 1H NMR (DMSO-d6): δ 8.41 (dd, 1H, J=1.7 and 4.7 Hz), 8.10 (s, 1H), 7.90 (dd, 1H, J=1.7 and 7.6 Hz), 7.83 (app t, 1H, J=0.6 Hz), 7.72 (dd, 1H, J=0.6 and 8.8 Hz), 7.51 (dd, 1H, J=4.7 and 7.6 Hz), 7.48 (dd, 1H, J=1.7 and 8.8 Hz), 4.07 (s, 3H).LCMS: rt 6.73 min (A), purity 99%, MS (m/e) 244 (MH+).

後処理

  1. customwas prepared
  2. temperatureby heating
  3. concentrationconcentrate by flash silica gel column chromatography [
  4. customupon dry loading the concentrate
  5. customabsorbed on silica gel]

出典と根拠

ORDレコード
ord-43062d70b560433396f249dbc9166821
出典データセット
uspto-grants-2015_09
特許番号
US09145433B2

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